To a solution of methyl 3,5-dibromobenzoate (3.00 g, 10.2 mmol) and 4-fluoro-phenyl boronic acid (1.43 g, 10.2 mmol) in 2-methoxyethyl ether (60 ml) and ethanol (3 ml) was added Na2CO3 (saturated, 9 ml), followed by tetrakis(triphenylphosphine) palladium (0) (0.2 g). The mixture was heated at 88° C. for 1.5 h, then cooled to room temperature, partitioned between hexane and water, and the organic phase washed with brine, dried over anhydrous sodium sulfate, decanted, and the organic solution concentrated under reduced pressure. The residue was purified by silica gel chromatography (1% EtOAc in hexane) to yield methyl 3-bromo-5-(4-fluorophenyl)benzoate (intermediate XXXIVa, 0.725 g, 23%) as a white solid, and methyl 3,5-di(4-fluorophenyl)benzoate (intermediate XXXIVb, 0.128 g, 4%) as a white solid.
