4-Chlorophenol → 1-Chloro-4-(4-methoxyphenoxy)benzene

HRID 274913Notes

Reaction equation

HRID 274913 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([O:17][C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 77304-BromoanisoleHCID 11430Potassium Carbonate

Product 1

HCID 101054561-Chloro-4-(4-methoxyphenoxy)benzene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 4-bromoanisole (35 ml, 0.28 mol), 4-chlorophenol (43 g, 0.33 mol), anhydrous K2CO3 (13 g, 0.09 mol) and copper bronze (0.38 g, 5.98 mmol) were stirred under a nitrogen atmosphere at 210° C. for 2 hours. After cooling to room temperature, the mixture was dissolved in methylene chloride, extracted two times with 1 N NaOH, dried (MgSO4) and the solvent removed under reduced pressure to give a brown liquid. Excess 4-bromoanisole was removed by distillation under reduced pressure (60°-73° C., 1 mm) and the residual crystalline solid was purified by HPLC (hexane-methylene chloride). 4-Methoxy-4'-chlorodiphenyl ether was isolated as a white crystalline solid (28.84 g, 44%), mp 49°-51° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted two times with 1 N NaOH
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customto give a brown liquid
  6. customExcess 4-bromoanisole was removed by distillation under reduced pressure (60°-73° C., 1 mm)
  7. customthe residual crystalline solid was purified by HPLC (hexane-methylene chloride)

Sources & evidence

ORD record
ord-d80948b0a8ca4512aecf3149e266d47c
Source dataset
uspto-grants-1995_02
Patent number
US05391571

Reaction notes

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