N-bromobutanimide → Ethyl 2-bromo-4-(bromomethyl)thiazole-5-carboxylate

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Reaction Steps

A mixture of 2-Bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester (5.67 g, 22.68 mmole), N-bromosuccinimide (4.44 g, 24.95 mmole) and benzoyl peroxide (275 mg, 1.13 mmole) in carbon tetrachloride (25 ml) was refluxed for 16 h before it was cooled to room temperature and partitioned between dichloromethane and water, the organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a white solid (4.46 g): MS: (+) m/z 337.80, 329.93, 331.93 (M+1, 79Br/81Br).

Provenance & Evidence