Phenol → 3-Bromodiphenyl ether

HRID 972007Notes

Reaction equation

HRID 972007 reaction equation
C[O-].[Na+].[C:4]1([OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=1>CO.COCCOCCOC>[Br:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:10][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 79271,3-DibromobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 961653-Bromodiphenyl etherYield 38.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8150DiglymeSolvent

Procedure

To a stirred mixture of 23 g sodium methylate in 69 g methanol and 200 ml of 2-methoxyethyl ether (diglyme) at room temperature was added dropwise 40.0 g of phenol in a period of 1/2 hour. The reaction mixture was then heated to 165°, and 5.0 g cuprous bromide was added. The reaction mixture was cooled to 150° and 100.0 g of 1,3-dibromobenzene was added rapidly. Upon complete addition, the reaction mixture was warmed to 165° and stirred for 24 hours. The reaction mixture was then allowed to cool to room temperature and filtered. The filter cake was washed with two 75 ml portions of chloroform. The filtrate was dried with sodium sulfate and filtered. Chloroform was evaporated from the filtrate under reduced pressure, leaving a residue. The residue was distilled under reduced pressure to give 40.5 g of 1-bromo-3-phenoxybenzene; bp, 98°-100°/0.5 mm. The nmr and the ir spectra were consistent with the assigned structure.

Workup

  1. temperatureThe reaction mixture was then heated to 165°
  2. temperatureThe reaction mixture was cooled to 150°
  3. additionUpon complete addition
  4. temperaturethe reaction mixture was warmed to 165°
  5. filtrationfiltered
  6. washThe filter cake was washed with two 75 ml portions of chloroform
  7. dry with materialThe filtrate was dried with sodium sulfate
  8. filtrationfiltered
  9. customChloroform was evaporated from the filtrate under reduced pressure
  10. customleaving a residue
  11. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-e5f52cdc67ec47f78f7a7de5294aef66
Source dataset
uspto-grants-1979_07
Patent number
US04162366

Reaction notes

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