N-Bromosuccinamide → 5-(Bromomethyl)-2-(4-nitrophenyl)oxazole

Participants

Reaction Steps

To a stirred solution of 5-methyl-2-(4-nitrophenyl)oxazole (3.2 g, 15.68 mmol) and benzoyl peroxide (10 mg, catalytic) in carbon tetrachloride (20 mL), was added N-bromo succinamide (2.77 g, 15.68 mmol). The mixture was heated to reflux for 9 h, filtered and the residue was washed with carbon tetrachloride. The combined filtrates were washed with water, sodium bicarbonate solution, brine, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified over silica gel (60-120 mesh) with 30% ethyl acetate/hexane as eluent to afford 5-(bromomethyl)-2-(4-nitro-phenyl)-oxazole (2.9 g, 65%) as a solid.

Provenance & Evidence