Bromine → 2-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:22]=[CH:21][C:14]3[N:15]=[N:16][N:17]([CH:18]([CH3:20])[CH3:19])[C:13]=3[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[Br:23]Br>C(O)(=O)C>[Br:23][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:9]([C:11]1[CH:22]=[CH:21][C:14]2[N:15]=[N:16][N:17]([CH:18]([CH3:19])[CH3:20])[C:13]=2[CH:12]=1)=[O:10]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 191 mg of 2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone in 2 mL of acetic acid was added 0.64 mL of bromine (1 M in acetic acid). The mixture was heated at 50° C. for 3 hours. The reaction mixture was cooled to 22° C. and concentrated to dryness. The residue was taken-up into ethyl acetate and washed with saturated aqueous sodium bicarbonate, brine; the organic layer was dried (sodium sulfate), filtered and the filtrate was concentrated to give 222 mg of 2-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone as a light yellow oil. This material was used without further purification.