Methanol → (2-Bromopyridin-3-yl)methanol

Participants

Reaction Steps

To a 2 L round bottom flask (fitted with stir bar, under nitrogen and at 0° C.) containing 2-bromo-3-pyridine-carboxaldehyde (22.15 g, 119.08 mmol) and methanol (200 mL), is added sodium borohydride (1.35 g, 35.72 mmol) in three portions. After 1 h at 0° C. water (200 mL) is added and the reaction is concentrated under reduced pressure to remove the methanol. The resulting residue is dissolved in ethyl acetate and washed with water (200 mL). The organic extraction is washed with brine, dried over magnesium sulfate, filtered and concentrated to afford 22 g of (2-bromo-3-pyridyl)methanol as a white solid. MS (m/z): 188 (M+1), 190 (M+3).

Provenance & Evidence