N-bromobutanimide → N-benzoyl-5-(bromomethyl)indole

Participants

Reaction Steps

A suspension of the product of Step A (5.5 g 23.4 mmol) in 10 mL of CCl4 was heated to reflux. N-bromosuccinimide (4.6 g, 25.7 mmol) and several crystals (approximately 100 mg) of azoisobutyronitrile (AIBN) were added. The resultant solution was stirred at reflux for 4 hours. The solution was cooled, diluted with 1.5 L of CH2Cl2 and washed with 400 mL of H2O and 400 mL of brine. The organic phase was dried over MgSO4, filtered and concentrated to a brown oil. The resultant oil was flash chromatographed eluting with 10:1 hexane/ethyl acetate to afford the titled compound (5.6g, 80%) as a yellow powder.

Provenance & Evidence