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

HRID 1110657Notes

Reaction equation

HRID 1110657 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 1N 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 1N 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-6c734cefce64484499d178a44cd021c7
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

Loading…