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

Participants

Reaction Steps

To a solution of 5-(4-methylphenyl)isoxazole (4.0 g, 25.13 mmol) in carbon tetrachloride (125 mL), N-bromosuccinimide (4.47 g, 25.13 mmol) and benzoyl peroxide (0.12 g, 0.50 mmol) were added. The resulting mixture refluxed for 1 h. After this time, the raction mixture was then cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by silica gel chromatography eluting with hexanes/EtOAc to give the title compound, 5-(4-(bromomethyl)phenyl)isoxazole, 4.2 g as an off-white solid. 1H NMR (CDCl3): δ 8.30 (d, J=2.2 Hz, 1H), 7.78 (d, J=8.3 Hz, 2H), 7.50 (d, J=8.3 Hz, 2H), 6.54 (d, J=1.7 Hz, 1H), 4.51 (s, 2H).

Provenance & Evidence