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

Participants

Reaction Steps

To a solution of 5-(4-methylphenyl)-isoxazole (17 g) and N-bromosuccinimide (19 g) in tetrachlormethane (500 ml) under nitrogen, bisbenzoyl peroxide (0.43 g) is added, and the mixture heated on reflux over night. The solvent is evaporated, and the residue purified by flash chromatography (silica gel, hexane/ethyl acetate 4:1) to give pure 5-(4-bromomethylphenyl)-isoxazole. NMR (CDCl3, 400 MHz) δ [ppm] 8.32 (d, 1.8 Hz, 1H), 7.78 (d, 8.2 Hz, 2H), 7.51 (d, 8.2 Hz, 2H), 6.54 (d, 1.8 Hz, 1H), 4.52 (s, 2H).

Provenance & Evidence