Benzoyl Peroxide → 2-(Bromomethyl)-4,5-dimethyl-1,3-oxazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4,5-trimethyloxazole (0.50 mL, 4.3 mmol), N-bromosuccinimide (0.77 g, 4.3 mmol) and benzoyl peroxide (0.21 g, 0.86 mmol) in carbon tetrachloride (4 mL) was heated at 76° C. under nitrogen atm for 3 hrs. After cooling to rt, the solid was removed by filtration. The filtrate solution was washed with saturated aqueous NaHCO3 (20 mL) and concentrated. The residue was purified by flash column chromatography (SiO2 ; hexanes:ethyl acetate/4:1) to afford 2-(bromomethyl)-4,5-dimethyloxazole (64 mg) as an yellow oil. 1H NMR (CDCl3) 67 4.4 (s, 2 H), 2.25 (s, 3 H), 2.05 (s, 3 H).

Provenance & Evidence