Water → 1-Chloro-4-(4-nitrophenoxy)benzene

HRID 1033761Notes

Reaction equation

HRID 1033761 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=CC=[CH:14][C:13]=1O.O.C([O:23][CH2:24][CH3:25])(=O)C>CS(C)=O>[Cl:11][C:12]1[CH:17]=[CH:25][C:24]([O:23][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72452-ChlorophenolHCID 8857Ethyl AcetateHCID 9590p-Fluoronitrobenzene

Product 1

HCID 157861-Chloro-4-(4-nitrophenoxy)benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 10.5 g (75.0 mmole) of 1-fluoro-4-nitrobenzene in 100 ml of dimethylsulfoxide and 9.64 g (75 mmole) of chlorophenol in 100 ml of DMSO was heated to 70° C. and maintained at this temperature for 4 hours. After allowing to cool to room temperature, 250 ml of water and then 250 ml of ethyl acetate were added slowly. The layers were separated and the organic layer was washed with 5×b 250 ml of water and 100 ml of sodium chloride, orange solid. Flash chromatography (CH2Cl2 eluent) yielded 18.34 g (98.0%) of the desired product as a yellow-orange solid.

Workup

  1. temperaturemaintained at this temperature for 4 hours
  2. customThe layers were separated
  3. washthe organic layer was washed with 5×b 250 ml of water and 100 ml of sodium chloride, orange solid

Sources & evidence

ORD record
ord-295d2ea3e874498c9713077d12bbb6e3
Source dataset
uspto-grants-1994_05
Patent number
US05312830

Reaction notes

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