Sodium borohydride → (5-Bromopyridin-2-yl)methanol

Participants

Reaction Steps

The commercially available 5-bromopyridine-2-carbaldehyde (2.0 g, 10.8 mmol) was dissolved in methanol (60 mL) and solid sodium borohydride (407 mg, 10.8 mmol) was added at 20° C. The reaction was stirred 30 minutes then the solvent was removed and 25 mL of saturated ammonium chloride solution was added and the reaction was extracted with 200 mL EtOAc which was washed with water and brine, 30 mL each. The organic phase was dried over magnesium sulfate and filtered through a 2 cm silica gel pad. The clear filtrate was concentrated by rotary evaporation to give a white solid, 1.99 g which was used as is.

Provenance & Evidence