N-bromobutanimide → 4-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

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A mixture of 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester (1.00 g, 3.18 mmol), N-bromosuccinimide (594 mg, 3.34 mol) and benzoyl peroxide (77 mg, 0.32 mmol) in carbon tetrachloride (15 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 yellow oil (1.32 g, product is 80% pure by 1H NMR, impurities are starting material and dibromonated compound); MS: (+) m/z 393.9, 395.9 (M+1, 79Br/81Br).

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