Water → 3-(4-Bromophenoxy)propan-1-ol

HRID 1978698Notes

Reaction equation

HRID 1978698 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][CH2:18][OH:19].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH2:17][CH2:18][OH:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 187610183-(4-Bromophenoxy)propan-1-olYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In DMF (150 ml) was dissolved 4-bromophenol (25 g). To the mixture was added potassium carbonate (30 g) and then was added dropwise 3-bromopropanol (26.1 g), and the mixture was stirred at 100° C. for 20 hours and cooled to room temperature. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=2/1) to give 3-(4-bromophenoxy)-1-propanol (20.6 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-e09eeea972b04994a721e0664aa50fba
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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