General procedure for the synthesis of 1-(6-bromo-3-fluoropyridin-2-yl)ethanol from 1-(6-bromo-3-fluoropyridin-2-yl)ethanone: 8.74 g (39.7 mmol) of 1-(6-bromo-3-fluoropyridin-2-yl)ethanol was dissolved in 175 mL of dichloromethane at room temperature, followed by the addition of 21.4 g (99.0 mmol) of chloro chromic acid pyridinium and 7.50 g of diatomaceous earth. The reaction mixture was stirred at room temperature for 25 hours before being filtered through the diatomaceous earth and washed with dichloromethane. The dichloromethane in the filtrate was concentrated and the residue was purified by fast chromatography (using 220 g of silica gel, eluent 0 to 10% hexane solution of ethyl acetate) to afford the target product 1-(6-bromo-3-fluoropyridin-2-yl)ethanone (6.82 g, 79% yield).LCMS (condition A): retention time t R = 2.11 min, mass-to-charge ratio m/e = 218 (M + H).
