3-Bromoaniline → HCID 57516629, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromophenylamine (2.78 g, 16.2 mmol) and 3-oxabicyclo[3.1.0]hexane-2,4-dione (2.0 g, 17.8 mmol) were suspended in 90 mL dichloromethane. The reaction was stirred at 50° C. for 3 h. The reaction was cooled to room temperature and 1,1′-carbonyldiimidazole (3.14 g, 19.4 mmol) was added in portions. The reaction was heated again to 50° C. and stirred overnight then cooled to room temperature and the solvent was evaporated. The residue was redissolved in 90 mL 1,2-dichloroethane and additional 1,1′-carbonyldiimidazole (1.13 g, 7.0 mmol) was added. The reaction mixture was heated at reflux for 2.5 h then cooled to room temperature. The solvent was evaporated and the product was crystallized from isopropyl alcohol to give 4.25 g (99%) of 3-(3-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-2,4-dione as a white solid.

Provenance & Evidence