4-Fluoroaniline → 5-Chloro-N-(4-fluorophenyl)-2-nitroaniline

HRID 2245322Notes

Reaction equation

HRID 2245322 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[F:14][C:15]1[CH:21]=[CH:20][C:18](N)=[CH:17][CH:16]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][C:18]2[CH:20]=[CH:21][C:15]([F:14])=[CH:16][CH:17]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 222822075-Chloro-N-(4-fluorophenyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

50 g of 1-chloro-3,4-dinitrobenzene in 250 ml of ethanol is mixed with 50 ml of 4-fluoroaniline and stirred for 35 hours at 60° C. After concentration by evaporation to half the volume, water and dichloromethane are divided up. After the organic phase is washed with 1N aqueous hydrochloric acid, it is dried on sodium sulfate, filtered and concentrated by evaporation. After chromatography on silica gel, 62.33 g (5-chloro-2-nitrophenyl)-(4-fluorophenyl)amine is obtained.

Workup

  1. concentrationAfter concentration
  2. customby evaporation to half the volume, water and dichloromethane
  3. washAfter the organic phase is washed with 1N aqueous hydrochloric acid, it
  4. customis dried on sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-02c047cdf6fe4e9883af7e2ca409dc42
Source dataset
uspto-grants-2010_03
Patent number
US07683081B2

Reaction notes

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