Benzoyl Peroxide → Ethyl 5-(bromomethyl)oxazole-2-carboxylate

Participants

Reaction Steps

To a stirred solution of ethyl 5-methyloxazole-2-carboxylate (5.1 g, 32.87 mmol) and NBS (8.19 g, 46.02 mmol) in carbon tetrachloride (50.0 mL), is added benzoyl peroxide (0.79 g, 3.29 mmol) and the reaction mixture is refluxed for 16 hours. The mixture is cooled to room temperature and filtered through diatomaceous earth. The filtrate is concentrated in vacuum and the crude is purified by silica gel chromatography, eluting with hexane:ethyl acetate (9.2:0.8) to give (4.8 g, 62.33%) of the title compound as a light brown oil. ESI/MS m/z (79Br/81Br) 234.1/236.1 [M+H]+.

Provenance & Evidence