N-bromobutanimide → HCID 86619641, compound

Participants

Reaction Steps

To a solution of dimethyl 2,3-dimethylmaleate (500 mg, 2.90 mmol) in carbon tetrachloride (11 mL) were added N-bromosuccinimide (803 mg, 4.51 mmol) and 2,2′-azobisisobutyronitrile (3.2 mg, 0.019 mmol) at room temperature, and the mixture was heated under reflux with stirring for 4 h. The reaction mixture was directly filtrated, and the filtrate was washed with water and brine. The residue obtained by concentrating the organic layer under reduced pressure was subjected to silica gel column chromatography (hexane-ethyl acetate 20:1→8:1) to give 191 mg of dimethyl 2-bromomethyl-3-methylmaleate (yield: 26%).

Provenance & Evidence