Toluene → 4-Biphenylcarboxylic acid, 4'-chloro-

Participants

Reaction Conditions

Reaction Steps

4-Chlorophenylboronic acid (501 mg) was combined with 4-iodobenzoic acid (795 mg), cesium carbonate (5.22 g), toluene (16 mL), water (8 mL) and n-butanol (4 mL). The mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (40 mg) was added. The reaction was heated to 80° C. for 20 hours after which, it was cooled to room temperature and diluted with ethyl acetate (16 mL). The solids were collected on a Celite pad and washed with hot methanol. The methanol filtrate was concentrated to dryness giving 4′-chloro-4-biphenylcarboxylic acid (305 mg). Yield=41%

Provenance & Evidence