Method for producing aromatic and heteroaromatic carboxylic acids, carboxylic acid esters and carboxylic acid amides

US8703992B2 · kind B2 · utility

Assignee

• BASF SE

Inventors

• Nina Challand · Mannheim, DE
• Ansgar Gereon Altenhoff · Heidelberg, DE
• Joachim Schmidt-Leithoff · Mannheim, DE
• Kathrin Wissel-Stoll · Ludwigshafen, DE
• Michael Rack · Eppelheim, DE
• Joachim Rheinheimer · Ludwigshafen, DE

Key dates

• Filing date: May 25, 2009
• Grant date: Apr 22, 2014
• Expiry date: Jun 13, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C67/36
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Process for the preparation of aromatic and heteroaromatic carboxylic acids, carboxylic acid esters and carboxamides by the reaction of aromatic or heteroaromatic halides R—Xn, in which n=integer from 1 to 6, R=substituted or unsubstituted and aromatic or heteroaromatic radical and X=chlorine, bromine or iodine atom, with carbon monoxide and water, ammonia, alcohols or amines in the presence of bases and zero-valent or divalent palladium compounds and bidentate diphosphanes or complexes of zero-valent or divalent palladium with bidentate diphosphanes, in which use is made of bidentate diphosphanes(R1—)(R2—)P—Y—P(—R3)(—R4)in which R1 to R4=unsubstituted aryl radicals or aryl radicals substituted with at least one radical exhibiting a positive resonance effect or a positive inductive effect, or unsubstituted or substituted cycloalkyl radicals, and Y=hydrocarbon group with a total of 2 to 20 carbon atoms, in which at least one of the carbon atoms carries only one or no hydrogen atom as substituent; except for the reaction of 4-bromo-3-difluoromethyl-1-methylpyrazole with 2-(3,4,5-trifluorophenyl)aniline and carbon monoxide to give N-[2-(3,4,5-trifluorophenyl)phenyl]-3-difluoromethyl-1…