3-Bromoaniline → HCID 57516629, compound

Temperature

50 °C

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.

1. temperatureThe reaction was cooled to room temperature
2. temperatureThe reaction was heated again to 50° C.
3. stirringstirred overnight
4. temperaturethen cooled to room temperature
5. customthe solvent was evaporated
6. dissolutionThe residue was redissolved in 90 mL 1,2-dichloroethane
7. temperatureThe reaction mixture was heated
8. temperatureat reflux for 2.5 h
9. temperaturethen cooled to room temperature
10. customThe solvent was evaporated
11. customthe product was crystallized from isopropyl alcohol

ORD record

ord-bf5fed507cc34e70bfeda74acff83acd

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2