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

Participants

Reaction Steps

N-Bromosuccinimide (0.91 g, 5.1 mmol) was added to a solution of ethyl 2-methyl-thiazole-5-carboxylate (0.8 g, 4.7 mmol) in carbon tetrachloride. The resultant reaction mixture was stirred for one hour whilist being illuminated by a photoflood lamp. After removing the solvent from the reaction mixture the resultant material was partitioned between ethyl acetate and water. The organic phase was then separated off, dried (MgSO4) and the evaporated. Chromatography on silica, eluting with 30% ethyl acetate in hexane, gave ethyl 2-(bromomethyl)-1,3-thiazole-5-carboxylate (490 mgs), NMR: δH (300 MHz, DMSO-d6, 1.20–1.38 (3 H,t); 4.20–4.37 (2 H,q); 5.05 (2 H, s); 8.55 (1 H, s).

Provenance & Evidence