m-Chloroperbenzoic acid → 1-Acetyl-4-bromoindolin-3-one

HRID 1882219Notes

Reaction equation

HRID 1882219 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

HCID 70297m-Chloroperbenzoic acidHCID 534157881-Acetyl-4-bromo-1H-indole-3-carbaldehyde

Product 1

HCID 532432881-Acetyl-4-bromoindolin-3-oneYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. washThe solution was washed with sat. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. stirringThe residue was stirred with K2CO3 (100 mg) in MeOH (50 mL) for 2 min
  5. concentrationThe solution was concentrated
  6. custompurified by silica gel chromatography (100% CH2Cl2)

Sources & evidence

ORD record
ord-a753f2890abc4f0ba6f7caa1d5869d7c
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

Loading…