A suspension of 4-bromo-1-fluoro-2-iodobenzene (420 mg, 1.39 mmol), 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 500 mg, 1.53 mmol), 2M aqueous sodium carbonate solution (2.5 mL) and dioxane (10 mL) was degassed with nitrogen for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.07 mmol) was added and the reaction warmed to 110° C. and stirred for 1 hour. The reaction was cooled to room temperature, diluted with water (10 mL), extracted with EtOAc (2×10 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified using silica gel column chromatography eluting with heptanes/EtOAc 7/3 to afford the title compound as a pale yellow solid in 73% yield, 418 mg.
