Diethyl Ether → 3-Bromo-5-chloro-2-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

A solution of bromine (1.5 mL, 29.28 mmol) in glacial acetic acid (7 mL) was slowly added to a mixture of 5-chloro-2-methoxypyridine (2.1 g, 14.63 mmol) and sodium acetate (1.2 g, 14.63 mmol) in glacial acetic acid (7 mL) and the resulting mixture was stirred at 80° C. for 6 hours. The reaction was allowed to cool down to ambient temperature and then diethyl ether and water were added. The organic layer was separated, washed with a 1N aqueous solution of sodium hydroxide and a 4% aqueous solution of sodium bisulphite, dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was purified by flash chromatography (100% hexanes) to give the title compound (2.1 g, 64%) as a white solid.

Provenance & Evidence