3-Bromo-4-chloro-N-methoxy-N-methylbenzamide (1.0 mg, 3.8 mmol, 1.0 eq) and 4-chloro phenyl boronic acid (787 mg, 5 mmol, 1.3 eq) was dissolved in toluene and stirred for 10 minutes. The solution was purged with nitrogen for 10 minutes and degassed under vacuum. Tetrakis triphenylphosphinepalladium (223 mg, 0.19 mmol, 0.05 eq) and K2CO3 (696 mg, 5 mmol, 1.3 eq) were added to the reaction. The mixture was refluxed for 12 h under nitrogen and the volatiles were removed under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel (60-120) eluting with 5-10% ethyl acetate/hexane to afford the desired compound (1 g, 90%). 1H NMR (400 MHz, CD3OD) δ 3.37-3.39 (s, 3H), 3.60-3.64 (s, 3H), 7.10-7.13 (t, 1H), 7.25-7.27 (t, 1H), 7.43-7.48 (m, 3H), 7.60-7.63 (m, 3H). MS (ESI): 310.2 (M+).
