Bromine → 849630-82-6
Reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[C:9]2=[O:14])([CH3:3])[CH3:2].[Br:15]Br>C(O)(=O)C>[Br:15][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1)[NH:11][C:10](=[O:13])[C:9]2=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
7-isopropylindoline-2,3-dione (23.8 g, 0.12 mol) was added to a stirred solution of glacial acetic acid (700 ml). To this solution was added, via additional funnel bromine (7.8 ml, 0.15 mol) in glacial acetic acid (300 ml) during 30 min. After the addition, the combined mixture was stirred at 75° C. for 3 hr, cooled, and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, and evaporated in vacuo; air dried to give (31.8 g, 94%) of crude product. 1H NMR (300 MHz, CDCl3) δ 8.04 (b, NH), 7.59 (dd 2H), 2.84 (m, 1H), 1.31 (d, 6H); ESI (+) MS m/e=269 (MH+), ESI (−) MS m/e=267 (MH−).