In a schlenk flushed with Argon were added methyl 4-chloro-3-(methylsulfonyl)benzoate (124.34 mg; 0.50 mmol; 1 eq.), o-tolylboronic acid (84.97 mg; 0.62 mmol; 1.25 eq.), palladium(II) acetate (22.45 mg; 0.10 mmol; 0.20 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (82.11 mg; 0.20 mmol; 0.40 eq.), potassium fluoride (87.14 mg; 1.50 mmol; 3 eq.), toluene (2.49 mL), MeOH (2.49 mL) and water (5.40 μl). The reaction was degassed with Ar and heated under reflux for 2 hours. Then, it was cooled down to RT. The solvents were evaporated and the crude mixture was dissolved in EtOAc, washed with water and brine and dried over MgSO4. The resulting crude product was purified by flash chromatography (c-hex/EtOAc 9:1 to 5:5), affording the title compound as a light yellow oil (135 mg; 88%). 1H NMR (DMSO-d6, 300 MHz) δ 8.89 (d, J=1.77 Hz, 1H), 8.32 (dd, J=1.77, 7.90 Hz, 1H), 7.43-7.19 (m, 5H), 4 (s, 3H), 2.76 (s, 3H), 2.09 (s, 3H). LC/MS (Method B): 305.1 (M+H)+. HPLC (max plot) 99.2%; Rt 4.51 min.
