4-Bromophenol → 2-(p-Bromophenoxy)ethanol

HRID 1582766Notes

Reaction equation

HRID 1582766 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][OH:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1

Participants

5

Conditions

Temperature
100 °C

Procedure

In a nitrogen atmosphere, 4-bromophenol 5.0 g, 2-bromoethanol 5.42 g, and potassium carbonate 12.0 g were added to N,N-dimethylformamide 30 ml, and the mixture was stirred at 100° C. After 1 hour, the mixture was cooled to room temperature and partitioned by adding water and diethyl ether. The organic layer was washed with water and brine, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 5.15 g, 82% was obtained as a colorless crystalline.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. custompartitioned
  3. additionby adding water and diethyl ether
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate anhydride
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 5.15 g, 82%
  8. customwas obtained as a colorless crystalline

Sources & evidence

ORD record
ord-186d08fcbda94dd48eed4a2bbf628914
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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