p-Bromochlorobenzene → 1-Chloro-4-(4-methoxyphenoxy)benzene

HRID 1591002Notes

Reaction equation

HRID 1591002 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=1.[OH-].[K+]>[Cu]>[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([O:15][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 90154-MethoxyphenolHCID 14797Potassium Hydroxide

Product 1

HCID 101054561-Chloro-4-(4-methoxyphenoxy)benzeneYield 53.7%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

4-Bromochlorobenzene (3.8 g), hydroquinone monomethyl ether (3.1 g) and potassium hydroxide (1.5 g) and copper powder (0.1 g) were mixed and the reaction was carried out at 160° C. to 200° C. for 3 hours. After cooling to room temperature, the reaction mixture was extracted with benzene (100 ml) and washed with 1 N sodium hydroxide, water, and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure and the residue was purified by medium pressure column chromatography using silica gel, to obtain 4-(4-chlorophenoxy)phenol methyl ether (2.5 g).

Workup

  1. extractionthe reaction mixture was extracted with benzene (100 ml)
  2. washwashed with 1 N sodium hydroxide, water, and saturated aqueous sodium chloride
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customthe residue was purified by medium pressure column chromatography

Sources & evidence

ORD record
ord-64a9e94bc4674a37b6f68560bdfbc43a
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

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