N-bromobutanimide → 2-Acetyl-4-bromo-7-methoxyfuro[2,3-c]pyridine

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Reaction Steps

A solution of 2-acetyl-7-methoxyfuro[2,3-c]pyridine (1.1 g) in acetonitrile (50 ml) was stirred at room temperature. N-Bromosuccinimide (1.0 g) was added and stirring continued overnight. The reaction was quenched by the addition of water (50 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were washed with water (50 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 33% ethyl acetate in hexane gave the title compound (1.4 g) as a white solid.

Provenance & Evidence