1,1'-Carbonyldiimidazole → 7-Iodo-5-nitro-1,3-benzoxazol-2(3H)-one

Participants

Reaction Steps

A solution of tert-butyl (2-hydroxy-3-iodo-5-nitrophenyl)carbamate (1.0 g, 2.6 mmol) and N,N-carbonyldiimidazole (0.47 g, 2.9 mmol) in THF (6 mL) was stirred at reflux for 1 h. The reaction mixture was concentrated, diluted with ethyl acetate (100 mL), washed with 1 N HCl (50 mL), water (20 mL), and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude solid. This material was concentrated from hexanes (2×) to give the desired product (5.7 g, 91%) as an orange solid. This material was purified by flash column chromatography to give the desired product (0.66 g, 82%) as a yellow solid. LCMS for C7H41N2O4 (M+H)+: m/z=306.8.

Provenance & Evidence