Diethyl Ether → 2-(5-Bromo-3-pyridyl)propan-2-ol

Participants

Reaction Steps

To a solution of 5-bromo-nicotinoyl chloride (900 mg, 4.1 mmol) in THF (18 mL) at −78° C. was added a 3.0 M solution of methylmagnesium bromide in diethyl ether (5.44 mL, 16.3 mmol). The reaction was stirred for 20 minutes and then quenched with saturated aqueous ammonium chloride. The reaction was then brought to room temperature, diluted with brine and ethyl acetate and the layers were separated. The aqueous layer was extracted two additional times with ethyl acetate, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 100%) to afford 2-(5-bromo-pyridin-3-yl)-propan-2-ol; MS: (ES+) m/z 216.0 (M+H)+.

Provenance & Evidence