Water → 6-Bromo-2-methoxynicotinaldehyde

Participants

Reaction Steps

A solution of 6-bromo-3-iodo-2-methoxypyridine (1.0 g) in diethyl ether (38 mL) was cooled to −80° C. in a nitrogen atmosphere, and n-butyllithium (2.6 M, 0.735 mL) were added dropwise. After stirring at the same temperature for one hour, N,N-dimethylformamide (0.62 mL) was added dropwise. The mixture was stirred at the same temperature for one hour and water was added to the reaction system, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=94:6→9:1) to give 6-bromo-2-methoxynicotinaldehyde as a colorless powder (618 mg, 90%).

Provenance & Evidence