4-Bromoaniline → HCID 6420877, compound

Participants

Reaction Steps

A solution of 4-bromoaniline (10.0 g, 58.1 mmol) in tetrahydrofuran (230 mL) was treated with sodium bicarbonate (9.77 g, 116.2 mmol) and water (100 mL) followed by isobutyl chloroformate (8.3 mL, 63.9 mmol), and the mixture was stirred at ambient temperature for 2 hrs. The mixture was then diluted with water (100 mL) and EtOAc (100 mL), the layers were separated, and the organic phase was washed with water (50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Recrystallization of the resulting solid from EtOAc/hexanes provided the title compound, mp 95-96° C.; MS (ESI−) for C11H14NO2Br m/z 270 (M−H)−.

Provenance & Evidence