Potassium Carbonate → 1-(3-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of trifluoro-methanesulfonic acid 4-acetyl-3-methyl-phenyl ester (6.10 g, 21.61 mmol) in dioxane/water (150/30 mL) is added 4-(trifluoromethyl)phenylboronic acid (4.51 g, 23.77 mmol), potassium carbonate (4.48 g, 32.42 mmol) and the reaction mixture is degassed with nitrogen for 20 min. Tetrakis(triphenylphosphine)palladium (1.25 g, 1.08 mmol) is added and the reaction mixture is heated to 80° C. overnight. TLC (10% EtOAc/hexane) indicates complete consumption of starting material. The reaction mixture is concentrated and chromatographed (330 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (5.77 g, 96%). 1NMR (400 MHz, CDCl3) δ ppm: 7.82 (d, 1H, J=7.9 Hz), 7.72 (s, 4H), 7.51-7.46 (m, 2H), 2.63 (s, 3H), 2.62 (s, 3H).

Provenance & Evidence