Water → 1-[2-(Benzyloxy)ethoxy]-4-bromobenzene

HRID 2220634Notes

Reaction equation

HRID 2220634 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([O:11][CH2:10][CH2:9][O:8][C:7]1[CH:12]=[CH:13][C:4]([Br:3])=[CH:5][CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 991682-(p-Bromophenoxy)ethanol

Product 1

HCID 139048991-[2-(Benzyloxy)ethoxy]-4-bromobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 0.500 g) was added to a solution of 2-(4-bromophenoxy)ethanol (2.25 g) in N,N-dimethylformamide (15 mL) at room temperature with stirring. After being stirred for 20 minutes, benzyl bromide (1.42 mL) was added at that temperature, and the mixture was stirred for additional 13 hrs. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to afford 1-(2-benzyloxyethoxy)-4-bromobenzene (2.51 g).

Workup

  1. stirringAfter being stirred for 20 minutes
  2. stirringthe mixture was stirred for additional 13 hrs
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-99ce46fde5d14fd2a017061b52f533af
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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