Benzoyl Peroxide → Ethyl 4-(bromomethyl)-3-(pyridin-4-yl)isoxazole-5-carboxylate

Participants

Reaction Steps

Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate (5.1 g, 22.0 mmol), NBS (4.7 g, 26.4 mmol), and benzoyl peroxide (0.53 g, 2.2 mmol) were added to 140 mL of carbon tetrachloride and the mixture was refluxed for 16 h. Solvent was removed in vacuo and the crude product was purified by flash chromatography (10-60% EtOAc/hexanes) to afford 1.5 g of the title compound. MS: (+) m/z 311, 313 (M+1, 79Br/81Br).

Provenance & Evidence