N-bromobutanimide → HCID 15594786, compound

Participants

Reaction Steps

Ethyl 2-fluorocrotonate (6.0 g) (prepared according to E. D. Bergmann and I. Shahak, J. Chem. Soc., 4033, 1961) N-bromosuccinimide (8.1 g) and benzoyl peroxide (0.15 g) was dissolved in carbon tetrachloride (120 ml) and heated at reflux for 3-5 hours. The mixture was cooled, filtered and the filtrate evaporated to dryness under reduced pressure. Chromatography on silica eluting with 10% diethyl ether:hexane gave ethyl 4-bromo-2-fluorocrotonate as a yellow oil (7.6 g). NMR 1H: 1.5(3H,t), 4.1(2H,dd), 4.4(2H,q), 6.4(1H,dt).

Provenance & Evidence