Water → 1-Bromo-4-(4-methoxybutoxy)benzene

HRID 1816770Notes

Reaction equation

HRID 1816770 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12]Br)=[CH:4][CH:3]=1.C[O-].[Na+].O.[C:18](OCC)(=[O:20])C>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:20][CH3:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 80633591-Bromo-4-(4-bromobutoxy)benzeneHCID 10942334Sodium Methoxide

Product 1

HCID 224947841-Bromo-4-(4-methoxybutoxy)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1-bromo-4-(4-bromobutoxy)benzene (3.05 g) in methanol (30 ml) was treated with 28% sodium methoxide in methanol (2.43 ml), and the solution was refluxed for 5 hours. After cooling, the reaction mixture was added to a mixture of water and ethyl acetate. The organic layer was washed with brine. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (10:1 hexane-ethyl acetate elution) to give 1-bromo-4-(4-methoxybutoxy)benzene (1.95 g).

Workup

  1. temperaturethe solution was refluxed for 5 hours
  2. temperatureAfter cooling
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (10:1 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-ae6c01ae7a1746f598f9c460ab58f3f5
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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