4-Chlorophenol → 1-Chloro-2-(4-nitrophenoxy)benzene

HRID 263076Notes

Reaction equation

HRID 263076 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=1.ClC1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O.[Cu]>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:4][C:1]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 164081-Chloro-2-(4-nitrophenoxy)benzeneYield 83.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

56 g (0.400 mol) of potassium carbonate and 5.6 g of purified copper are added to a lukewarm solution (≃60° C.) of 51.5 g (0.400 mol) of p-chlorophenol and 72 g (0.456 mol) of p-chloronitrobenzene in 40 ml of dimethylformamide and the mixture is then heated to the reflux temperature for 5 hours. The inorganic salts are removed by filtering the reaction mixture and the dimethylformamide is evaporated under reduced pressure. The residue is purified by crystallisation from methanol to give 83.2 g of a yellow beige powder.

Workup

  1. temperaturethe mixture is then heated to the reflux temperature for 5 hours
  2. customThe inorganic salts are removed
  3. filtrationby filtering the reaction mixture
  4. customthe dimethylformamide is evaporated under reduced pressure
  5. customThe residue is purified by crystallisation from methanol

Sources & evidence

ORD record
ord-72c0bd01a252404292cd5d4c1d069b77
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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