N-bromobutanimide → HCID 68852787, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Bromo-2-methylphenyl)-4,5-dihydro-1,3-oxazole (0.33 g, 1.38 mmol, from Step A) was dissolved in carbon tetrachloride. AIBN (0.003 g) and N-bromosuccinimide (0.18 g, 4.14 mmol) were sequentially added, the mixture was degassed with argon for 5 min and then heated at 85° C. for 24 h. The reaction was filtered, diluted with methylene chloride (200 mL) and washed with saturated sodium bisulfite (2×100 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 3% ethyl acetate/hexanes yielded 60 mg of the desired product: 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=8.5 Hz, 1H), 7.49 (s, 1H), 7.45 (d, J=8.2 Hz, 1H), 7.16 (s, 1H), 2.67 (s, 3H).

Provenance & Evidence