Methanol → 2-Bromo-6-methoxypyridine

Participants

Reaction Steps

Dried sodium (970 mg, 42.2 mmol) was added portionwise to cooled methanol (50 ml) under nitrogen, and once addition was complete, 2,6-dibromopyridine (10 g, 42.2 mmol) was added portionwise. The resulting suspension was heated under reflux for 24 hours. The cooled reaction was concentrated under reduced pressure, the residue diluted with water (100 ml), and extracted with ethyl acetate (2×75 ml). The organic extracts were dried (MgSO4), and evaporated under reduced pressure to give a pale yellow oil. The crude product was purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (100:0 to 98:2) to give the title compound as a clear oil, 4.23 g.

Provenance & Evidence