Water → 1-(6-Bromo-2-methoxypyridin-3-yl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromo-3-iodo-2-methoxypyridine (500 mg) in diethyl ether (15 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-dimethylacetamide (0.37 mL) was added dropwise. The mixture was warmed to −40° C. over 1.5 hours to complete the reaction. Water and ethyl acetate was added to the reaction system. The organic layer was washed with brine and then 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=9:1→4:1) to give the title compound as a colorless powder (284 mg, 78%).

Provenance & Evidence