Water → 1-Bromo-4-(2-methoxyethyl)benzene

HRID 914483Notes

Reaction equation

HRID 914483 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I.O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 219957171-Bromo-4-(2-methoxyethyl)benzeneYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Bromophenyl)ethanol (2.0 g) was dissolved in N,N-dimethylformamide (50 mL), and sodium hydride (60% in oil) (0.44 g) was added under ice-cooling. After gradually warming to room temperature, the mixture was stirred for 2 hr, and methyl iodide (2.1 g) was added again under ice-cooling. After gradually warming to room temperature, the mixture was stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=20:1 to 10:1) to give the title compound (1.2 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperatureAfter gradually warming to room temperature
  4. stirringthe mixture was stirred overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-44db238a9a1f47a3a2e8ce4ed8014932
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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