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

HRID 44299Notes

Reaction equation

HRID 44299 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-6d6ce9bf124942cda9586ffa2fb7a844
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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