N-bromobutanimide → HCID 14098280, compound

Participants

Reaction Steps

To a solution of 5.99 g (45.0 mmoles) (1) in 135 ml carbon tetrachloride was added 8.81 g (49.5 mmoles) N-bromosuccinimide and 100 mg benzoyl peroxide. The mixture was refluxed while illuminated by a 250 watt sunlamp for 18 hours. The mixture was cooled and filtered, and the filtrate concentrated to give 9.9 g of a dark red oil. The oil was extracted with 500 ml hot hexane. The hexane solution was evaporated to 150 ml and cooled to give 6.60 g (69%) of crystalline (2), m.p. 51.0°-52.5°; nmr (deuteriochloroform): 4.6 (s, 2H), 7.2 (m, 3H), 9.3 (s, 1H).

Provenance & Evidence