Sodium Hydroxide → 5-Bromo-2-methoxypyridine

Participants

Reaction Steps

Bromine (0.99 ml) was added dropwise to a stirred suspension of sodium acetate (1.59 g) and 2-methoxypyridine (1.93 ml) in acetic acid (10 ml). The reaction mixture was stirred at room temperature for 25 minutes, then at 80° C. for 2.5 h. The mixture was then allowed to cool and poured into ice-water, neutralised with 2M sodium hydroxide and extracted with ether. The combined extracts were dried (MgSO4), filtered and evaporated. The crude product was purified by column chromatography on silica gel eluting with 5% ethyl acetate in hexane to give 5-bromo-2-methoxypyridine as a colourless oil (1.75 g, 51%).

Provenance & Evidence