Chlorosuccinimide → 1-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 1976785Notes

Reaction equation

HRID 1976785 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:14]N1C(=O)CCC1=O>C(#N)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][C:11]=2[Cl:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 7218471-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 186292691-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)ethan-1-oneYield 39.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-acetyl-5-bromo-indoline (1.20 g, 5 mmol) and N-chlorosucinimide (0.734 g, 5.5 mmol) in acetonitrile (80 mL) was heated to reflux for 12 hours, cooled to room temperature, and concentrated. The concentrate was purified by flash column chromatography on silica gel to provide 0.548 g of the desired product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. concentrationconcentrated
  4. customThe concentrate was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-e5345672241a408481abc3290b234514
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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