N-bromobutanimide → 2-Bromo-3,5-dimethoxypyridine

Participants

Reaction Steps

To a stirred solution of 3,5-dimethoxypyridine (780 mg, 5.6 mmol) in dry MeCN (24 ml) was added N-bromosuccinimide (1.0 g, 5.6 mmol) and the reaction was heated to reflux for 1 hour. After cooling, the solvent was removed under vacuum and the residue was triturated with diethyl ether to precipitate the succinimide by-product and filtered. The filtrate was concentrated onto silica-gel and the residue purified by flash chromatography (silica-gel, eluted with hexanes:EtOAc, 3:1) to afford the product as a white solid (860 mg, 70%). 1H-NMR (300 MHz, CDCl3) δ 7.67 (d, J=2.5 Hz, 1H), 6.71 (d, J=2.5 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H).

Provenance & Evidence