Acetyl chloride → 5-(2-Chloroacetyl)-6-fluoroindolin-2-one

HRID 241751Notes

Reaction equation

HRID 241751 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][C:11](=[O:15])[NH:12]2)=[CH:8][CH:7]=1.[C:16](Cl)(=[O:18])[CH3:17]>C(Cl)Cl>[Cl:1][CH2:17][C:16]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:6]=1[F:5])[NH:12][C:11](=[O:15])[CH2:10]2)=[O:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 37310136-fluoro-2,3-dihydro-1H-indol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 106093595-(2-Chloroacetyl)-6-fluoroindolin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

20 mL of DCM are added dropwise under nitrogen to aluminium chloride (31.1 mmol) at 0-5° C. 6-Fluoroindolin-2-one (5.18 mmol) and acetyl chloride (6.73 mmol) are added to the mixture. The reaction mixture is heated at 50° C. overnight. The reaction mixture is cooled to ambient temperature and then poured into an ice bath, and the suspension obtained is filtered and then washed with cold water to yield the title product.

Workup

  1. temperatureThe reaction mixture is cooled to ambient temperature
  2. additionpoured into an ice bath
  3. customthe suspension obtained
  4. filtrationis filtered
  5. washwashed with cold water

Sources & evidence

ORD record
ord-d78c29d352cb4bba84c7425fa3357d2b
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Reaction notes

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