Hydrogen Bromide → HCID 86592993, compound
Reaction equation
[BrH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14](=[O:16])[CH3:15])[N:11]=[C:10]2[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[CH:5][CH:4]=1.BrBr.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:1][CH2:15][C:14]([C:12]1[N:11]=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)[CH:13]=1)=[O:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
Aqueous HBr (0.98 ml of a 48% solution) was added to a solution of 1-[1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazol-4-yl]-ethanone I-7f (1.60 g, 4.38 mmol) in acetic acid (20 ml). Bromine (0.226 ml, 4.38 mmol) was added next to the reaction mixture in a dropwise manner. The resultant orange solution was stirred at 23° C. for 1 h before warming to 40° C. for 40 min and then cooling to 23° C. for 60 h. The reaction mixture was poured into a mixture of ice and saturated aqueous sodium bicarbonate, and the resultant mixture was extracted with ethyl acetate (2 200-ml portions). The combined organics were washed with saturated aqueous sodium bicarbonate (100 ml) and were dried over anhydrous magnesium sulfate and concentrated to afford 2-bromo-1-[1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazol-4-yl]-ethanone I-7g (1.03 g, 53%).
Workup
- temperaturebefore warming to 40° C. for 40 min
- temperaturecooling to 23° C. for 60 h
- extractionthe resultant mixture was extracted with ethyl acetate (2 200-ml portions)
- washThe combined organics were washed with saturated aqueous sodium bicarbonate (100 ml)
- dry with materialwere dried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9a7d2e4f10994b10ba3d31af44bdb147
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07247628B2
Reaction notes
Loading…