Water → 4-Chloro-3-fluoroaniline

HRID 1245436Notes

Reaction equation

HRID 1245436 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

Into 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. After addition of water to the reaction solution, the system was extracted with chloroform. The chloroform layer was washed with saturated brine, dried on anhydrous magnesium sulfate and the solvent was distilled off. The resulting residue was separated and purified on silica gel column chromatography (hexane/ethyl acetate=5/1) to provide 21 g of the title compound.

Workup

  1. extractionthe system was extracted with chloroform
  2. washThe chloroform layer was washed with saturated brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe resulting residue was separated
  6. custompurified on silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-bcdf210c5883434dbba163d3b92df031
Source dataset
uspto-grants-2006_10
Patent number
US07125877B2

Reaction notes

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