N-bromobutanimide → Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

Participants

Reaction Steps

A solution of ethyl 2-methyl-4-thiazolecarboxylate [JCS 1946, 87, E. R. H. Jones, F. A. Robinson, M. N. Strachan] (5.0 g, 29.2 mmol) in CCl4 (30 ml) was treated with N-bromosuccinimide (5.2 g, 29.2 mmol) and benzoylperoxide (0.03 g). The reaction was heated to reflux while irradiating with a strong lamp for 21/2 hours. The reaction mixture was allowed to cool to ambient temperature, filtered and evaporated. The residue was purified by chromatography (eluant: CH2Cl2) to obtain ethyl 2-bromomethyl-4-thiazolecarboxylate (2.27 g, 31%).

Provenance & Evidence