Benzoyl Peroxide → 4-Bromomethyl-2-(methyl-phenyl-amino)-thiazole-5-carboxylic acid ethyl ester

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A mixture of 4-methyl-2-(methyl-phenyl-amino)-thiazole-5-carboxylic acid ethyl ester (3.32 g, 12.0 mmol), N-bromosuccinimide (2.35 g, 13.2 mol) and benzoyl peroxide (291 mg, 1.2 mmol) in carbon tetrachloride (45 mL) was refluxed for 17 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. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow oil: MS: (+) m/z 354.9, 356.9 (M+1, 79Br/81Br).

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