4-Bromophenol → 1-Bromo-4-((6-bromohexyl)oxy)benzene

HRID 1816685Notes

Reaction equation

HRID 1816685 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][Br:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 123681,6-Dibromohexane

Product 1

HCID 224947501-Bromo-4-((6-bromohexyl)oxy)benzeneYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-bromophenol (10 g), 1,6-dibromohexane (49.4 g) and potassium carbonate (9.59 g) in N,N-dimethylformamide (50 ml) was stirred for 4 hours at 60° C. (bath temp.), and then cooled to ambient temperature. To the reaction mixture was added ethyl acetate (200 ml), and the mixture was washed with water (200 ml×2) and brine. The organic layer was dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude product. The crude product was purified by silica gel chromatography (1:0-1:1 hexane-ethyl acetate) to give 1-bromo-4-(6-bromohexyloxy)benzene (15.61 g).

Workup

  1. temperaturecooled to ambient temperature
  2. washthe mixture was washed with water (200 ml×2) and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationMagnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customto give a crude product
  7. customThe crude product was purified by silica gel chromatography (1:0-1:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-20ecb62ac1ad4b3387cfedd5b1a06f08
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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