Boron tribromide → 1-(2-Hydroxy-5-(trifluoromethyl)phenyl)ethan-1-one

Participants

Reaction Steps

To a stirred solution of 1-[2-methoxy-5-(trifluoromethyl)phenyl]ethanone (35 g, 0.16 mol) in dry dichloromethane (400 mL) at 0° C. was added solid tetrabutylammonium iodide (2.96 g, 0.008 mol) followed by boron tribromide (33.96 mL, 0.35 mol) drop-wise. After addition, the reaction mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was cooled to 0° C. and quenched with ice. The mixture was extracted with diethyl ether (1 L). The organic layer was washed with water (2 L) and then saturated aqueous sodium chloride (1 L). After concentration of the organic layer at ambient temperature in vacuo, the crude product was purified by silica gel column chromatography (2% diethyl ether in hexane elution) to afford the title compound as a colourless oil (11.5 g, 35%).

Provenance & Evidence