Water → 4-Chloro-3-fluoroaniline

HRID 1064367Notes

Reaction equation

HRID 1064367 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Cl:9]N1C(=O)CCC1=O.O>ClCCl>[Cl:9][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 962WaterHCID 97423-FluoroanilineHCID 31398Chlorosuccinimide

Product 1

HCID 27365114-Chloro-3-fluoroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 96 ml of 3-fluoroaniline in 1000 ml of dichloromethane, 147 g of N-chlorosuccinimide was added at 0° C. and stirred for 12 hours at room temperature. Water was added to the reaction solution which then was extracted with chloroform. The extract was washed with saturated brine, dried on anhydrous sodium sulfate and distilled. The residue was separated and purified on silica gel column chromatography (hexane/ethyl acetate=5/1) to provide 21 g of the title compound as a yellow solid.

Workup

  1. extractionthen was extracted with chloroform
  2. washThe extract was washed with saturated brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. distillationdistilled
  5. customThe residue was separated
  6. custompurified on silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-b065334bc68449228924ee3bfa905706
Source dataset
uspto-grants-2005_11
Patent number
US06969712B2

Reaction notes

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