N-bromobutanimide → 2-Bromomethyl-5-iodo-benzofuran

Participants

Reaction Steps

To a carbon tetrachloride (28 mL) solution of 5-iodo-2-methylbenzofuran (500 mg, 1.94 mmol) were added N-bromosuccinimide (410 mg, 2.3 mmol) and 2,2-azobis(isobutyronitrile) (47.8 mg, 0.291 mmol). This mixture was stirred for 2 hours and 45 minutes while heating under reflux. After allowing the reaction mixture to cool on standing, the reaction mixture was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 2-bromomethyl-5-iodo-benzofuran (320 mg, 49%).

Provenance & Evidence