2-Bromopyridine → 2-[(2,5-Difluorophenyl)-hydroxymethyl]pyridine

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Reaction Steps

A hexane solution (1.53M, 3.92 ml, 0.6 mmol) of n-butyl lithium was added dropwise to a tetrahydrofuran (10 ml) solution of 2-bromopyridine (572 μl, 6 mmol) under an argon atmosphere at −78° C., followed by stirring for 30 minutes. To the resulting brown solution was added dropwise 2,5-difluorobenzaldehyde (655 μl, 6 mmol) and the temperature of the reaction mixture was gradually raised to room temperature. To the reaction mixture was added water. The resulting mixture was then extracted with ethyl acetate. After the solvent was dried, the residue obtained by concentration under reduced pressure was purified by purification by silica gel chromatography to give the title compound (120 mg, 9%) as a white solid.

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