Water → 3-Bromo-5-methoxypyridine

Participants

Reaction Steps

3,5-Dibromopyridine (30.0 g) was added to a stirred solution of sodium methoxide (prepared from 11.6 g of sodium) in methanol (120 ml) and heated to reflux for 70 hours under an atmosphere of nitrogen. The mixture was cooled to ambient temperature, poured into water (1 l), extracted with diethyl ether (three times) and the extracts combined, washed with water (four times) and dried (magnesium sulphate). The solvent was evaporated under reduced pressure to give 3-bromo-5-methoxypyridine as a colourless liquid, 19.3 g, which slowly crystallised on storing.

Provenance & Evidence