Potassium Carbonate → 3-(3-Fluorophenyl)-5-fluorobenzoic acid

Participants

Reaction Steps

A 2 dram vial was charged with (3-fluorophenyl)boronic acid (168 mg, 1.2 mmol), 3-chloro-5-fluorobenzoic acid (175 mg, 1.0 mmol), potassium carbonate (345 mg, 2.5 mmol), palladium acetate (1.1 mg, 0.005 mmol) and 2-dicyclohexylphosphino-2,6-dimethoxy-3-sulfonato-1,1′-biphenyl hydrate sodium salt (5 mg, 0.01 mmol). The vial was fitted with a septum cap, degassed water (1.5 mL) was added and the mixture was purged with nitrogen and stirred at room temperature. After stirring for 4 d, the mixture was diluted with water (30 mL), acidified to pH 4 with 1.0 N aqueous HCl and extracted with EtOAc (3×25 mL). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 235 mg (quant.) of 3′,5-difluoro-[1,1′-biphenyl]-3-carboxylic acid which was used without further purification.

Provenance & Evidence