m-Chloroperbenzoic acid → 1-Acetyl-4-bromoindolin-3-one
Reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([Br:13])[CH:9]=[CH:10][CH:11]=2)[C:6](C=O)=[CH:5]1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([Br:13])[CH:9]=[CH:10][CH:11]=2)[C:6](=[O:24])[CH2:5]1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Acetyl-4-bromo-1H-indole-3-carbaldehyde (3.5 g, 13.2 mmol) was dissolved in CH2Cl2 (50 mL). 3-Chloroperbenzoic acid (3.9 g, 15.8 mmol) was added, and the reaction stirred 16 h at r.t. The solution was washed with sat. NaHCO3 and brine, dried (MgSO4), and concentrated. The residue was stirred with K2CO3 (100 mg) in MeOH (50 mL) for 2 min. The solution was concentrated and purified by silica gel chromatography (100% CH2Cl2) to give 880 mg (26%) of the title compound as a faintly blue solid. MS (ES) [m+H] calc'd for C10H8BrNO2, 254, 256; found 254, 256.