Ethyl Acetate → 6-Bromo-3-pyridinemethanol

Participants

Reaction Steps

1.34 ml (1.34 mmol) of a 1 M solution of lithium aluminum hydride in THF are initially introduced into 5 ml dry THF under argon, and a solution of 500 mg (2.69 mmol) 6-bromo-3-pyridinecarbaldehyde in 3 ml dry THF is added dropwise at 0° C. The mixture is subsequently stirred at RT for 1 h, 25 ml ethyl acetate are then added, while cooling in an ice bath, and hydrolysis is carried out slowly with 50 ml saturated sodium bicarbonate solution. The aqueous phase is extracted with ethyl acetate (three times with 20 ml each time). The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated on a rotary evaporator. After removal of solvent residues in vacuo, 375 mg (74% of th.) of the title compound are obtained.

Provenance & Evidence