Hydrochloric Acid → 2-Fluoro-3-(3-fluorophenyl)-5-methyl-benzoic acid

Participants

Reaction Steps

A mixture of 3-bromo-2-fluoro-5-methyl-benzoic acid (400 mg, 1.7 mmol, 1.0 eq), (3-fluorophenyl)boronic acid (720 mg, 5.2 mmol, 3.0 eq), K2CO3 (356 mg, 2.6 mmol, 1.5 eq) and Pd(PPh3)4 (396.0 mg, 0.40 mmol, 0.2 eq) in acetonitrile (5 mL) and H2O (4 mL) was heated at reflux overnight. The reaction was acidified to pH 3 by addition of 1M HCl and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as a solid (160 mg, 75%).

Provenance & Evidence