METHOD FOR AROMATIC FLUORINATION

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species.

METHOD FOR AROMATIC FLUORINATION

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. 1. A fluorination method comprising: 'where Ar is an aryl or heteroaryl;', 'providing a compound having the structure Ar—OH to a reaction mixture;'}{'sub': 2', '2, 'providing SOFto the reaction mixture;'}providing a fluorinating reagent to the reaction mixture;{'sub': 2', '2, 'reacting the SOF, the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.'}2. The fluorination method of claim 1 , wherein the fluorinating reagent is selected from the group consisting of sodium fluoride claim 1 , potassium fluoride claim 1 , cesium fluoride claim 1 , tetrabutylammonium fluoride claim 1 , and tetramethylammonium fluoride.3. A method according to claim 1 , further comprising providing a solvent to the reaction mixture.4. The fluorination method of claim 3 , wherein the solvent is selected from the group consisting of polar aprotic solvents claim 3 , alkoxy ether solvents claim 3 , nitrile solvents claim 3 , aromatic solvents claim 3 , and mixtures thereof.5. The fluorination method of claim 4 , wherein the solvent comprises a polar aprotic solvent.6. The fluorination method of claim 4 , wherein the solvent comprises an alkoxy ether solvent.7. The fluorination method of claim 4 , wherein the solvent comprises a nitrile solvents.8. The fluorination method of claim 4 , wherein the solvent comprises an aromatic solvent.9. The fluorination method of claim 3 , wherein the fluorinating reagent is selected from the group consisting of sodium fluoride claim 3 , potassium fluoride claim 3 , cesium fluoride claim 3 , tetrabutylammonium fluoride claim 3 , and tetramethylammonium fluoride.10. The fluorination method of claim 4 , wherein the fluorinating reagent is selected from the ...

COMPOSITE POLYAMIDE MEMBRANE TREATED WITH DIHYROXYARYL COMPOUNDS AND NITROUS ACID

A method for making a composite polyamide membrane comprising a porous support and a polyamide layer, including the steps of: i) applying a polar solution including a polyfunctional amine monomer and a non-polar solution including a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a polyamide layer; ii) applying a dihydroxyaryl compound to the polyamide layer, wherein the dihydroxyaryl compound is represented by: formula wherein D, D′, D″ and D′″ are independently selected from: alkyl, alkoxy, hydrogen, halogen, hydroxyl and amine, and L is a linking group; and iii) exposing the thin film polyamide layer to nitrous acid. 2. The method of wherein steps i) claim 1 , ii) and iii) are performed sequentially.3. (canceled)4. (canceled)5. (canceled)6. The method of wherein D claim 1 , D′ claim 1 , D″ claim 1 , and D′″ are hydrogen.7. (canceled)8. The method of wherein E and E′ are independently selected from: amide and ether.9. The method of wherein the non-polar solution further comprises an acid-containing monomer comprising a C-Chydrocarbon moiety substituted with at least one carboxylic acid functional group or salt thereof and at least one amine-reactive functional group selected from: acyl halide claim 1 , sulfonyl halide and anhydride claim 1 , wherein the acid-containing monomer is distinct from the polyfunctional acyl halide monomer10. The method of wherein the thin film polyamide layer has a dissociated carboxylic acid content of at least 0.18 moles/kg at pH 9.5 as measured by RBS prior to the step of exposing the thin film polyamide layer to nitrous acid.12. The method of wherein the dihydroxyaryl compound is selected from at least one of:N,N′-(benzene-1,3-diyldimethanediyl)bis(3,5-dihydroxybenzamide)N,N′-(1,4-phenylenebis(methylene))bis(3,5-dihydroxybenzamide)N,N′-[5-(trifluoromethyl)benzene-1,3-diyl]bis(3,5-dihydroxybenzamide)N,N′-biphenyl-4,4′-diylbis(3,5-dihydroxybenzamide)N,N′-ethane-1,2 ...

COMPOSITE POLYAMIDE MEMBRANE INCLUDING CELLULOSE-BASED QUATERNARY AMMONIUM COATING

thin film composite membrane comprising a thin film polyamide layer located between a porous support and a coating layer, wherein the coating layer comprises a cellulose-based polymer including a plurality of quaternary ammonium groups or salts thereof.

METHOD FOR AROMATIC FLUORINATION

Disclosed is a f fluorination method comprising providing a fluorinating reagent and a solvent to a reaction mixture; providing a compound having the formula Ar—X to the reaction mixture; wherein, A is a aryl, substituted aryl, heteroaryl or substituted heteroaryl, and X is CI, Br, I or NO, providing tetramethylammonium 2,6-dimethylphenolate to the reaction mixture; and reacting under conditions sufficient to provide a species having the formula Ar—F. 1. A fluorination method comprising:providing a solvent to a reaction mixture;providing a fluorinating reagent to the reaction mixture; A is a aryl, substituted aryl, heteroaryl or substituted heteroaryl, and', {'sub': '2', 'X is Cl, Br, I or NO,'}], 'wherein, 'providing a compound having the formula Ar—X to the reaction mixture;'}providing a tetraalkyl ammonium phenolate salt to the reaction mixture; andreacting under conditions sufficient to provide a species having the formula Ar—F.2. The fluorination method of claim 1 , wherein the solvent s a polar aprotic solvent.3. The fluorination method of claim 1 , wherein A is iso-propyl 5-chloro-6-phenylpicolinate; 2-chloroquinoline claim 1 , (4-nitrophenyl)(phenyl)methanone.4. The fluorination method of claim 1 , wherein the reaction temperature is from 0 to 130 degrees C.5. The fluorination method of claim 1 , wherein the reaction mixture includes 1 equivalent of the Ar—X claim 1 , 2 to 3 equivalents of tetramethylammonium 2 claim 1 ,6-dimethylphenolate claim 1 , 3 to 10 equivalents of the fluorinating reagent.6. The fluorination method of claim 2 , wherein the polar aprotic solvent comprises DMF claim 2 , NMP claim 2 , DMSO claim 2 , DMPU claim 2 , or DMAC.7. The fluorination method of claim 4 , wherein the reaction temperature is from 25 to 130 degrees C.8. The fluorination method of claim 1 , wherein the tetraalkyl ammonium phenolate salt is tetramethylammonium 2 claim 1 ,6-dimethylphenolate.9. The fluorination method of claim 1 , wherein the reaction mixture does not ...

PROCESSES FOR THE PREPARATION OF 4-ALKOXY-3-(ACYL OR ALKYL)OXYPICOLINAMDES

A fungicidal 4-methoxy-3-acetyloxypicolinamide may be conveniently prepared in processes that include the coupling together of 4-methoxy-3-acetyloxypicolinic acid or 4-methoxy-3-hydroxypicolinic acid with a key 2-aminopropanoate ester derived from a 1,1-bis(4-fluorophenyl)propane-1,2-diol. 2. The process of wherein the acylating agent is an alkyl chloroformate of the Formula ClCOR claim 1 , wherein R is a C-Calkyl or benzyl claim 1 , or an acid chloride of the Formula RCOCl claim 1 , wherein R is a C-Calkyl.3. The process of wherein the chlorinating agent is oxalyl chloride or thionyl chloride.4. The process of wherein the base may be selected from the group including triethylamine (TEA) claim 1 , diisopropylethylamine (DIPEA) claim 1 , pyridine claim 1 , potassium carbonate claim 1 , and mixtures thereof.5. The process of wherein the first mixture further comprises a solvent selected from the group including dichloromethane (DCM) claim 1 , 1 claim 1 ,2-dichloroethane (DCE) claim 1 , isopropyl acetate claim 1 , tetrahydrofuran (THF) claim 1 , 2-MeTHF claim 1 , acetonitrile (ACN) claim 1 , and mixtures thereof.7. The process of wherein the acylating agent is an alkyl chloroformate of the Formula ClCOR claim 6 , wherein R is a C-Calkyl or a benzyl.8. The process of wherein the first mixture further comprises a solvent selected from the group including dichloromethane (DCM) claim 6 , 1 claim 6 ,2-dichloroethane (DCE) claim 6 , acetonitrile (ACN) claim 6 , isopropyl acetate claim 6 , THF claim 6 , 2-MeTHF claim 6 , and mixtures thereof.9. The process of wherein the first base may be selected from the group including triethylamine (TEA) claim 6 , diisopropylethylamine (DIPEA) claim 6 , pyridine and potassium carbonate.10. The process of wherein about 3 equivalents of the first base and about 2 equivalents of the acylating agent are used.11. The process of wherein the alkali metal base may be selected from the group including LiOH claim 6 , NaOH claim 6 , KOH claim 6 , ...

METHOD FOR COUPLING A FIRST COMPOUND TO A SECOND COMPOUND

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture including a base, the base comprising a carbonate salt, a phosphate salt or an acetate salt, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound in the presence of a mild base. 1. A method of coupling a first compound to a second compound , method comprising:providing the first compound having a fluorosulfonate substituent, the first compound comprising an aryl or a heteroaryl group;providing the second compound comprising an amine; andreacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture including a base, the base comprising a carbonate salt, a phosphate salt or an acetate salt, the reaction mixture under conditions effective to couple the first compound to the second compound.2. The method of claim 1 , wherein the reaction mixture further includes a ligand.3. The method of wherein the catalyst is generated in-situ from a palladium precatalyst.4. The method of wherein the catalyst is generated in-situ from a palladium precatalyst claim 1 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 1 , Palladium(II) chloride claim 1 , Dichlorobis(acetonitrile)palladium(II) claim 1 , Dichlorobis(benzonitrile)palladium(I1) claim 1 , Allylpalladium chloride dimer claim 1 , Palladium(II) acetylacetonate claim 1 , Palladium(II) bromideBis(dibenzylideneacetone) ...

METHOD FOR COUPLING A FIRST AROMATIC COMPOUND TO A SECOND AROMATIC COMPOUND

In one aspect, there is provided a method of coupling a first aromatic compound having a fluorosulfonate substituent to a second aromatic compound having a boron-containing substituent. In another aspect, there is provided a method of coupling a first aromatic compound having a hydroxyl substituent to a second aromatic compound having a boron-containing substituent in a one-pot reaction. 1. A method of coupling a first aromatic compound to a second aromatic compound , the method comprising:providing the first aromatic compound having a fluorosulfonate substituent; 'reacting the first aromatic compound and the second aromatic compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first aromatic compound to the second aromatic compound.', 'providing the second aromatic compound having a boron-containing substituent; and'}2. The method of claim 1 , wherein the reaction mixture further includes a ligand claim 1 , and a base.3. The method of claim 1 , wherein at least one of the first aromatic compound or the second aromatic compound is heteroaryl.4. The method of wherein the catalyst is a palladium catalyst or a nickel catalyst.5. The method of claim 4 , wherein the catalyst is generated in-situ from a palladium precatalyst claim 4 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 4 , Palladium(II) chloride claim 4 , Dichlorobis(acetonitrile)palladium(II) claim 4 , Dichlorobis(benzonitrile)palladium(II) claim 4 , Allylpalladium chloride dimer claim 4 , Palladium(II) acetylacetonate claim 4 , Palladium(II) bromide claim 4 , Bis(dibenzylideneacetone)palladium(0) claim 4 , Bis(2-methylallyl)palladium chloride dimer claim 4 , Crotylpalladium chloride dimer claim 4 , Dichloro(1 claim 4 ,5-cyclooctadiene)palladium(II) claim 4 , Dichloro(norbornadiene)palladium(II) claim 4 , Palladium(II) trifluoroacetate claim 4 , ...

METHOD FOR COUPLING A FIRST COMPOUND TO A SECOND COMPOUND

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound. 1. A method of coupling a first compound to a second compound , the method comprising:providing the first compound having a fluorosulfonate substituent, the first compound comprising an aryl or a heteroaryl group;providing the second compound comprising an amine; andreacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.2. The method of claim 1 , wherein the reaction mixture further includes a ligand.3. The method of wherein the catalyst is generated in-situ from a palladium precatalyst.4. The method of wherein the catalyst is generated in-situ from a palladium precatalyst claim 3 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 3 , Palladium(II) chloride claim 3 , Dichlorobis(acetonitrile)palladium(II) claim 3 , Dichlorobis(benzonitrile)palladium(II) claim 3 , Allylpalladium chloride dimer claim 3 , Palladium(II) acetylacetonate claim 3 , Palladium(II) bromide claim 3 , Bis(dibenzylideneacetone)palladium(0) claim 3 , Bis(2-methylallyl)palladium chloride dimer claim 3 , Crotylpalladium chloride dimer claim 3 , Dichloro(1 claim 3 ,5-cyclooctadiene)palladium(II) claim 3 , Dichloro(norbornadiene)palladium(II) claim 3 , Palladium(II) ...

METHOD FOR COUPLING A FIRST COMPOUND TO A SECOND COMPOUND

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound. 1. A method of coupling a first compound to a second compound , the method comprising:{'sub': '2', 'providing the first compound having a fluorosulfonate substituent substituent of the formula —OSOF, the first compound comprising an aryl or a heteroaryl group;'}providing the second compound comprising an amine; andreacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.2. The method of claim 1 , wherein the reaction mixture further includes a ligand.3. The method of wherein the catalyst is generated in-situ from a palladium precatalyst.4. The method of wherein the catalyst is generated in-situ from a palladium precatalyst claim 1 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 1 , Palladium(II) chloride claim 1 , Dichlorobis(acetonitrile)palladium(II) claim 1 , Dichlorobis(benzonitrile)palladium(II) claim 1 , Allylpalladium chloride dimer claim 1 , Palladium(II) acetylacetonate claim 1 , Palladium(II) bromideBis(dibenzylideneacetone)palladium(0) claim 1 , Bis(2-methylallyl)palladium chloride dimer claim 1 , Crotylpalladium chloride dimer claim 1 , Dichloro(1 claim 1 ,5-cyclooctadiene)palladium(II) claim 1 , Dichloro(norbornadiene) ...

METHOD FOR AROMATIC FLUORINATION

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SOFto a reaction mixture; reacting the SOFand the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where A is an aryl or heteroaryl; providing SOFto the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SOF, the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F. 2. The fluorination method of claim 1 , wherein the solvent is selected from the group consisting of polar aprotic solvents claim 1 , alkoxy ether solvents claim 1 , nitrile solvents claim 1 , and aromatic solvents.3. The fluorination method of claim 1 , wherein the fluorinating reagent is selected from the group consisting of sodium fluoride claim 1 , potassium fluoride claim 1 , cesium fluoride claim 1 , lithium fluoride claim 1 , tetrabutylammonium fluoride claim 1 , and tetramethylammonium fluoride.5. The fluorination method of claim 4 , wherein the solvent is selected from the group consisting of polar aprotic solvents claim 4 , alkoxy ether solvents claim 4 , nitrile solvents claim 4 , and aromatic solvents.6. The fluorination method of claim 4 , wherein the cation is selected from the group consisting of claim 4 , sodium claim 4 , potassium claim 4 , cesium claim 4 , tetramethylammonium claim 4 , and tetrabutylammonium.7. A fluorination method comprising: 'where A is an aryl or heteroaryl;', 'providing a compound having the structure Ar—OH to a reaction mixture;'}{'sub': 2', '2, 'providing SOFto the reaction mixture;'} ...

METHOD FOR COUPLING AN AROMATIC COMPOUND TO AN ALKYNE

In one aspect, there is provided a method of coupling an aromatic compound having a fluorosulfonate substituent to an alkyne. In another aspect, there is provided a method of coupling an aromatic compound having a hydroxyl substituent to an alkyne in a one-pot reaction. 1. A method of coupling an aromatic compound to an alkyne , the method comprising:{'sub': '2', 'providing the aromatic compound having a fluorosulfonate substituent of the formula —OSOF;'}providing the alkyne; andreacting the aromatic compound and the alkyne in a reaction mixture, the reaction mixture including a catalyst comprising one or more of a group 10 atom and a copper complex, the reaction mixture under conditions effective to couple the aromatic compound to the alkyne.2. The method of claim 1 , wherein the reaction mixture further includes a ligand claim 1 , and a base.3. The method of claim 1 , wherein the aromatic compound is heteroaryl.4. The method of claim 1 , wherein the catalyst is one or more of a palladium catalyst or a nickel catalyst or a copper complex.5. The method of claim 4 , wherein the catalyst is generated in-situ from a palladium precatalyst claim 4 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 4 , Palladium(II) chloride claim 4 , Dichlorobis(acetonitrile)palladium(II) claim 4 , Dichlorobis(benzonitrile)palladium(II) claim 4 , Allylpalladium chloride dimer claim 4 , Palladium(II) acetylacetonate claim 4 , Palladium(II) bromide claim 4 , Bis(dibenzylideneacetone)palladium(0) claim 4 , Bis(2-methylallyl)palladium chloride dimer claim 4 , Crotylpalladium chloride dimer claim 4 , Dichloro(1 claim 4 ,5-cyclooctadiene)palladium(II) claim 4 , Dichloro(norbornadiene)palladium(II) claim 4 , Palladium(II) trifluoroacetate claim 4 , Palladium(II) benzoate claim 4 , Palladium(II) trimethylacetate claim 4 , Palladium(II) oxide claim 4 , Palladium(II) cyanide claim 4 , Tris(dibenzylideneacetone)dipalladium(0) claim 4 , Palladium(II) ...

METHOD FOR COUPLING AN AROMATIC OR VINYLIC COMPOUND TO A BORON-CONTAINING COMPOUND

In one aspect, there is provided a method of coupling an aromatic or vinylic compound having a fluorosulfonate substituent to a boron-containing compound. In another aspect, there is provided a method of coupling an aromatic or vinylic compound having a hydroxyl substituent to a boron-containing compound in a one-pot reaction. 1. A method of coupling an aromatic or vinylic compound to a boron-containing compound , the method comprising:providing the aromatic or vinylic compound having a fluorosulfonate substituent;providing the boron-containing compound; andreacting the aromatic or vinylic compound and the boron-containing compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the aromatic or vinylic compound to the boron-containing compound thereby forming a new carbon-boron bond between the aromatic or vinylic compound and the boron-containing compound.2. The method of claim 1 , wherein the reaction mixture further includes a ligand claim 1 , and a base.3. The method of claim 1 , wherein the aromatic or vinylic compound is heteroaryl.4. The method of wherein the catalyst is a palladium catalyst or a nickel catalyst.5. The method of claim 4 , wherein the catalyst is generated in-situ from a palladium precatalyst claim 4 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 4 , Palladium(II) chloride claim 4 , Dichlorobis(acetonitrile)palladium(II) claim 4 , Dichlorobis(benzonitrile)palladium(II) claim 4 , Allylpalladium chloride dimer claim 4 , Palladium(II) acetylacetonate claim 4 , Palladium(II) bromide claim 4 , Bis(dibenzylideneacetone)palladium(0) claim 4 , Bis(2-methylallyl)palladium chloride dimer claim 4 , Crotylpalladium chloride dimer claim 4 , Dichloro(1 claim 4 ,5-cyclooctadiene)palladium(II) claim 4 , Dichloro(norbornadiene)palladium(II) claim 4 , Palladium(II) trifluoroacetate claim 4 , Palladium( ...

METHOD FOR COUPLING A FIRST COMPOUND TO A SECOND COMPOUND

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. 1. A method of coupling a first compound to a second compound , the method comprising:{'sub': '2', 'providing the first compound having a fluorosulfonate substituent of the formula —OSOF;'}providing the second compound comprising an alkene; andreacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.2. The method of claim 1 , wherein the reaction mixture further includes a ligand.3. The method of wherein the catalyst is generated in-situ from a palladium precatalyst.4. The method of wherein the catalyst is generated in-situ from a palladium precatalyst claim 1 , the palladium precatalyst is selected from the group consisting of: Palladium(II) acetate claim 1 , Palladium(II) chloride claim 1 , Dichlorobis(acetonitrile)palladium(II) claim 1 , Dichlorobis(benzonitrile)palladium(II) claim 1 , Allylpalladium chloride dimer claim 1 , Palladium(II) acetylacetonate claim 1 , Palladium(II) bromideBis(dibenzylideneacetone)palladium(0) claim 1 , Bis(2-methylallyl)palladium chloride dimer claim 1 , Crotylpalladium chloride dimer claim 1 , Dichloro(1 claim 1 ,5-cyclooctadiene)palladium(II) claim 1 , Dichloro(norbomadiene)palladium(II) claim 1 , Palladium(II) trifluoroacetate claim 1 , Palladium(II) benzoate claim 1 , Palladium(II) trimethylacetate claim 1 , Palladium(II) oxide claim 1 , Palladium(II) ...

PROCESS FOR THE PREPARATION OF 4-ALKOXY-3-HYDROXYPICOLINIC ACIDS

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 2-hydroxypicolinonitrile in a series of chemical steps selected from chlorination, chloro substitution, nitrile hydrolysis and chloro reduction. 2. The process of wherein the solvent for the first mixture is selected from the group including water claim 1 , acetonitrile claim 1 , sulfolane claim 1 , DMSO and xylene.3. The process of wherein the chlorinating agent is selected from the group including chlorine claim 1 , sulfuryl chloride and 1 claim 1 ,3-dichloro-5 claim 1 ,5-dimethylhydantoin.4. The process of wherein Ris CH.5. The process of wherein the mineral acid is sulfuric acid.6. The process of wherein the strong base is sodium hydroxide or potassium hydroxide.7. The process of wherein the reducing agent is comprised of hydrogen and a transition metal catalyst.8. The process of wherein the hydrogen is hydrogen gas and the transition metal catalyst is comprised of palladium on carbon. The present disclosure concerns a process for the preparation of 4-alkoxy-3-hydroxypicolinic acids. More particularly, the present disclosure concerns a process for the preparation of 4-alkoxy-3-hydroxypicolinic acids from furfural.U.S. Pat. No. 6,521,622 B1 and U.S. application Ser. Nos. 61/747,723 and 14/142,183, the disclosures of which are hereby incorporated by reference in their entireties, describe inter alia certain heterocyclic aromatic amide compounds of general Formulaand their use as fungicides.These disclosures also describe the preparation of 4-alkoxy-3-hydroxypicolinic acids as key intermediates in the preparation of these heterocyclic aromatic amide compounds. It would be useful to have an efficient and scalable process route to 4-alkoxy-3-hydroxypicolinic acids from inexpensive raw materials.The present disclosure concerns processes for the preparation of 4-alkoxy-3-hydroxypicolinic acids of Formula AThe compound of Formula A may be prepared in a multi-step process which comprises the following ...

PROCESSES FOR THE PREPARATION OF 4-ALKOXY-3-(ACYL OR ALKYL)OXYPICOLINAMDES

A fungicidal 4-methoxy-3-acetyloxypicolinamide may be conveniently prepared in processes that include the coupling together of 4-methoxy-3-acetyloxypicolinic acid or 4-methoxy-3-hydroxypicolinic acid with a key 2-aminopropanoate ester derived from a 1,1-bis(4-fluorophenyl)propane-1,2-diol. 2. The process of wherein the acylating agent is an alkyl chloroformate of the Formula ClCOR claim 1 , wherein R is a C-Calkyl or benzyl claim 1 , or an acid chloride of the Formula RCOCl claim 1 , wherein R is a C-Calkyl.3. The process of wherein the chlorinating agent is oxalyl chloride or thionyl chloride.4. The process of wherein the base may be selected from the group including triethylamine (TEA) claim 1 , diisopropylethylamine (DIPEA) claim 1 , pyridine claim 1 , potassium carbonate claim 1 , and mixtures thereof.5. The process of wherein the first mixture further comprises a solvent selected from the group including dichloromethane (DCM) claim 1 , 1 claim 1 ,2-dichloroethane (DCE) claim 1 , isopropyl acetate claim 1 , tetrahydrofuran (THF) claim 1 , 2-MeTHF claim 1 , acetonitrile (ACN) claim 1 , and mixtures thereof.7. The process of wherein the acylating agent is an alkyl chloroformate of the Formula ClCOR claim 6 , wherein R is a C-Calkyl or a benzyl.8. The process of wherein the first mixture further comprises a solvent selected from the group including dichloromethane (DCM) claim 6 , 1 claim 6 ,2-dichloroethane (DCE) claim 6 , acetonitrile (ACN) claim 6 , isopropyl acetate claim 6 , THF claim 6 , 2-MeTHF claim 6 , and mixtures thereof.9. The process of wherein the first base may be selected from the group including triethylamine (TEA) claim 6 , diisopropylethylamine (DIPEA) claim 6 , pyridine and potassium carbonate.10. The process of wherein about 3 equivalents of the first base and about 2 equivalents of the acylating agent are used.11. The process of wherein the alkali metal base may be selected from the group including LiOH claim 6 , NaOH claim 6 , KOH claim 6 , ...

Process for the preparation of 4-alkoxy-3-hydroxypicolinic acids

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 2-hydroxypicolinonitrile in a series of chemical steps selected from chlorination, chloro substitution, nitrile hydrolysis and chloro reduction.

Method for aromatic fluorination

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO 2 F 2 to a reaction mixture; reacting the SO 2 F 2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO 2 F 2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO 2 F 2 , the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.

Method for coupling a first compound to a second compound

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

Process for the preparation of 4-alkoxy-3-hydroxypicolinic acids

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 2-hydroxypicolinonitrile in a series of chemical steps selected from chlorination, chloro substitution, nitrile hydrolysis and chloro reduction.

Processes for the preparation of 4-alkoxy - (acyl or aquyl) oxy-picolinamide.

PROCESOS PARA LA PREPARACIÓN DE 4-ALCOXI-3-(ACIL O ALQUIL)-OXIPICOLINAMIDAS. PROCESSES FOR THE PREPARATION OF 4-ALCOXI-3- (ACIL OR ALQUIL) -OXIPICOLINAMIDAS.

Method for aromatic fluorination

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO 2 F 2 to a reaction mixture; reacting the SO 2 F 2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where A is an aryl or heteroaryl; providing SO 2 F 2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO 2 F 2 , the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.

Composite polyamide membrane including cellulose-based quaternary ammonium coating

thin film composite membrane comprising a thin film polyamide layer located between a porous support and a coating layer, wherein the coating layer comprises a cellulose-based polymer including a plurality of quaternary ammonium groups or salts thereof.

Processes for the preparation of 4-alkoxy-3-(acyl or alkyl)oxypicolinamides

Method for aromatic fluorination

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO 2 F 2 to a reaction mixture; reacting the SO 2 F 2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO 2 F 2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO 2 F 2 , the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.

Method for coupling a first compound to a second compound

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture including a base, the base comprising a carbonate salt, a phosphate salt or an acetate salt, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound in the presence of a mild base.

Organopolysiloxane cluster polymer for rapid air uv cure

A composition contains a cluster organopolysiloxane having structure (I) where X = (aa) and R is independently in each occurrence selected from a group consisting of aryl groups and alkyl groups having from 2 to 6 carbons; R' and R" are independently in each occurrence selected from divalent hydrocarbon groups containing from 2 to 6 carbon atoms; n is a value in a range of 50 to less than 200; and A is independently in each occurrence selected from a group consisting of acrylate, methacrylate and trialkoxysilyl groups; provided that, on average, 50 to 95 mole-percent of the A groups are selected from acrylate and methacrylate groups and 5 to 50 mole-percent of the A groups are selected from trialkoxysilyl groups.

Método para acoplar un primer compuesto a un segundo compuesto

Método para acoplar un primer compuesto a un segundo compuesto, en donde el método comprende proporcionar un primer compuesto que tiene un sustituyente fluorosulfonato, proporcionar el segundo compuesto que comprende una amina; y hacer reaccionar el primer compuesto y el segundo compuesto en una mezcla de reacción, en donde la mezcla de reacción incluye un catalizador que tiene al menos un átomo del grupo 10, la mezcla de reacción incluye una base, en donde la base comprende una sal de carbonato, una sal de fosfato o una sal de acetato, en donde la mezcla de reacción está en condiciones eficaces para acoplar el primer compuesto al segundo compuesto. La presente descripción también describe un método en un recipiente para acoplar un primer compuesto a un segundo compuesto en presencia de una base ligera.

método para acoplar um primeiro composto a um segundo composto

a presente revelação descreve um método para acoplar um primeiro composto a um segundo composto, sendo que o método compreende: fornecer o primeiro composto que tem um substituinte de fluorossulfonato; fornecer o segundo composto que compreende uma amina; e reagir o primeiro composto e o segundo composto em uma mistura de reação, sendo que a mistura de reação inclui um catalisador que tem pelo menos um átomo do grupo 10, sendo que a mistura de reação inclui uma base, sendo que a base compreende um sal de carbonato, um sal de fosfato ou um sal de acetato; a mistura de reação sob condições eficazes para acoplar o primeiro composto ao segundo composto. a presente revelação descreve, adicionalmente, um método de um único recipiente para acoplar um primeiro composto a um segundo composto na presença de uma base suave.

método para acoplamento de um composto aromático a um alquino

num aspecto, é proporcionado um método para acoplar um composto aromático tendo um substituinte fluorossulfonato a um alquino. num outro aspecto, é proporcionado um método para acoplar um composto aromático tendo um substituinte hidroxil a um alquino em uma reação de um recipiente.

Organopolysiloxane cluster polymer for rapid air uv cure

A composition contains a cluster organopolysiloxane having structure (I) where X = (aa) and R is independently in each occurrence selected from a group consisting of aryl groups and alkyl groups having from 2 to 6 carbons; R' and R" are independently in each occurrence selected from divalent hydrocarbon groups containing from 2 to 6 carbon atoms; n is a value in a range of 50 to less than 200; and A is independently in each occurrence selected from a group consisting of acrylate, methacrylate and trialkoxysilyl groups; provided that, on average, 50 to 95 mole-percent of the A groups are selected from acrylate and methacrylate groups and 5 to 50 mole-percent of the A groups are selected from trialkoxysilyl groups.

Organopolysiloxane cluster polymer for rapid air uv cure

A composition contains a cluster organopolysiloxane having the following structure: where: and R is independently in each occurrence selected from a group consisting of aryl groups and alkyl groups having from 2 to 6 carbons; R′ and R″ are independently in each occurrence selected from divalent hydrocarbon groups containing from 2 to 6 carbon atoms; n is a value in a range of 50 to less than 200; and A is independently in each occurrence selected from a group consisting of acrylate, methacrylate and trialkoxysilyl groups; provided that, on average, 50 to 95 mole-percent of the A groups are selected from acrylate and methacrylate groups and 5 to 50 mole-percent of the A groups are selected from trialkoxysilyl groups.

Process for the preparation of 4-alkoxy-3-hydroxypicolinic acids

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 2-hydroxypicolinonitrile in a series of chemical steps selected from chlorination, chloro substitution, nitrile hydrolysis and chloro reduction.

Composite polyamide membrane treated with dihyroxyaryl compounds and nitrous acid

A method for making a composite polyamide membrane comprising a porous support and a polyamide layer, including the steps of: i) applying a polar solution including a polyfunctional amine monomer and a non-polar solution including a polyfunctional acyl halide monomer to a surface of a porous support and interfacially polymerizing the monomers to form a polyamide layer; ii) applying a dihydroxyaryl compound to the polyamide layer, wherein the dihydroxyaryl compound is represented by: formula wherein D, D′, D″ and D′″ are independently selected from: alkyl, alkoxy, hydrogen, halogen, hydroxyl and amine, and L is a linking group; and iii) exposing the thin film polyamide layer to nitrous acid.