Hydrochloric Acid → (2-Bromopyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-bromonicotinaldehyde (50 g, 0.27 mol), methanol (250 mL) and THF (250 mL) in a 3-necked round bottom flask at 0° C. was added sodium borohydride (10.3 g, 0.27 mol) portion wise. The reaction mixture was stirred at 0° C. for 1 hr and warmed up to room temperature. The reaction mixture was adjusted to pH 7 with 2N HCl (120 mL), and concentrated to remove methanol and THF. The resulting mixture was partitioned between EtOAc and brine three times. The organic layer was combined and washed with brine, dried over Na2SO4, and concentrated to give (2-bromopyridin-3-yl)methanol (51 g), which was used without further purification. LRMS (M+H+) m/z 187.9.

Provenance & Evidence