N-bromobutanimide → Ethyl 2-(bromomethyl)thiazole-5-carboxylate

Participants

Reaction Steps

A solution of ethyl 2-methyl-5-thiazole carboxylate [S. H Mashragui, P. M. Keehn, JACS 104 4461-4465 (1982)] (4.73 g, 27.68 mmol) in carbon tetrachloride (30 ml) was treated with N-bromosuccinimide (4.92 g, 27.64 mmol) and benzoyl peroxide (0.03 g). The reaction mixture was heated to reflux under a strong light for 11/4 hours. The reaction was allowed to cool to ambient temperature and filtered. The filtrate was evaporated and subjected to chromatography (CH2Cl2) to give the title product (1.16 g, 17%). NMR (200 MH2,DMSO-d6) : δ8.4 (s, 1H) , 5.06 (s, 2H) , 4.33 (g, 2H), 1.3 (t, 3H).

Provenance & Evidence