83 mg of 2-chloro-6-fluorophenylboronic acid, 0.10 g of sodium hydrogen carbonate, 0.6 mL of ethanol, 0.3 mL of wafer and 23 mg of tetrakis(triphenylphosphine)palladium(0) were added to 2.1 mL of toluene solution containing 0.15 g of tert-butyl 2-(benzamido)-4-bromobenzoate, and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, 21 mg of 2-chloro-6-fluorophenylboronic acid and 23 mg tetrakis(triphenylphosphine)palladium(0) were added and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, toluene and a saturated sodium, hydrogen carbonate aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=10:1] to obtain tert-butyl 2-(benzamido)-4-(2-chloro-6-fluorophenyl)benzoate.
