N-bromobutanimide → 2-Bromo-5-(3-methylphenyl)furan

Participants

Reaction Steps

A stirred solution of 10.0 g (0.063 mol) of 2-(3-methylphenyl)furan in 250 mL of carbon tetrachloride was heated to reflux, and 0.1 g of benzoyl peroxide was added. The solution was heated at reflux for ten minutes, then an additional 0.1 g of benzoyl peroxide followed by 11.2 g (0.063 mol) of N-bromosuccinimide, were added. Upon complete addition, refluxing was continued for an additional 18 hours. The reaction mixture was cooled, filtered, and the filtrate washed with 200 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 13.7 g of 2-bromo-5-(3-methylphenyl)furan.

Provenance & Evidence