N-Iodosuccinimide → 7-Iodo-4-(trifluoromethyl)-1H-indole-2,3-dione
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5](=[O:13])[C:6](=[O:12])[NH:7]2.[I:16]N1C(=O)CCC1=O>OS(O)(=O)=O>[I:16][C:9]1[CH:10]=[CH:11][C:3]([C:2]([F:1])([F:14])[F:15])=[C:4]2[C:8]=1[NH:7][C:6](=[O:12])[C:5]2=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 4-trifluoromethylisatin (450 mg, 2.09 mmol) and N-iodosuccinimide (800 mg, 3.72 mmol) in conc. H2SO4 (5 mL) was stirred for 6 h at 40° C. and poured into crushed ice. The mixture was extracted with ethyl acetate and the extracts were washed with aqueous Na2SO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate to give the title compound (296 mg, 42%).