Process for preparing biaryl compounds
AssigneeCatalytica Pharmaceuticals, Inc.
InventorsJoseph Arthur Miller, Robert Patrick Farrell
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Abstract
The present invention provides a process for preparing biaryl compounds comprising reacting an arylmetal reagent selected from arylmagnesium reagents and aryllithium reagents with an arylhalide in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a cocatalyst selected from zinc cocatalysts and cadmium cocatalysts. The present invention specifically provides a process for the preparation of 2-(4'-methylphenyl)benzonitrile comprising reacting a 4-methylphenylmagnesium reagent with a 2-halobenzonitrile in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a zinc cocatalyst.
Claims17
A process for the preparation of an biaryl compound of the formula Ar-Ar' comprising reacting an arylmetal reagent selected from arylmagnesium reagents and aryllithium reagents, wherein the aryl group is Ar, with an arylhalide of the formula Ar'X, wherein X is a halide, in the presence of a catalyst system consisting essentially of a catalyst selected from nickel catalysts and palladium catalysts and a cocatalyst selected from zinc cocatalysts and cadmium cocatalysts, and wherein the cocatalyst is present at a mole ratio of cocatalyst to aryl metal reagent of less than 1:4 and the mole ratio of cocatalyst to catalyst is in the range of 25:1 to 1:1.
A process for the preparation of 2-(4'-methylphenyl) benzonitrile comprising reacting a 4-methylphenylmagnesium reagent with a 2-halobenzonitrile in the presence of a catalyst system a consistently essentially of a catalyst selected from nickel catalysts and palladium catalysts and a zinc cocatalyst, and wherein the cocatalyst is present at a mole ratio of cocatalyst to 4-methylphenyl magnesium reagent of less than 1:4 and the mole ratio of cocatalyst to catalyst is in the range of 25:1 to 1:1.
In the process for the preparation of biaryl compounds by reacting an arylmetal reagent selected for arylmagnesium reagents and aryllithium reagents with an arylhalide in the presence of a catalyst selected from nickel catalysts and palladium catalysts, the improvement wherein the reaction mixture further consists essentially of a cocatalyst selected from zinc cocatalysts and cadmium cocatalysts, said cocatalyst being present at a mole ratio of cocatalyst to arylmetal reagent of less than 1:4 and with the mole ratio of cocatalyst to catalyst being in the range of 25:1 to 1:1.
Dependencies are inferred from the claim text.