Benzoyl Peroxide → 5-(4-(Bromomethyl)phenyl)isoxazole

Participants

Reaction Steps

Bisbenzoyl peroxide (560 mg, 0.232 mmol) is added to a solution of 2.17 g (13.65 mmol) of 5-(4-methyl-phenyl)-isoxazole (Lin, Y. -i.; Lang, Jr., S. A. J. Org. Chem. 1980, 45, 4857) and N-bromosuccinimide (2.43 g, 13.65 mmol) in 64 mL of CCl4, and the reaction mixture is heated at reflux overnight. The reaction mixture is then concentrated in vacuo, and the product is purified by chromatography on silica gel (20% EtOAC/hexane, Rf=0.6) to yield 5-(4-bromomethyl-phenyl)-isoxazole. 1H NMR (250 MHz., CDCl3) δ 8.30 (d, 1H), 7.73 (d, 2H), 7.45 (d, 2H), 6.51 (d, 1H), 4.50 (s, 2H).

Provenance & Evidence