2-Bromoethanol → 2-(3-BroMo-phenoxy)-ethanol

HRID 1582767Notes

Reaction equation

HRID 1582767 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][OH:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 105367272-(3-BroMo-phenoxy)-ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a nitrogen atmosphere, 3-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 reaction mixture was cooled to room temperature and partitioned by adding water and diethyl ether. The organic layer was washed with water and then with 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 (4.85 g, 77%) was obtained as a colorless oil.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. custompartitioned
  3. additionby adding water and diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialwith brine, dried over magnesium sulfate anhydride
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound (4.85 g, 77%)
  8. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-150c977ffbf2411da004a9b09b492068
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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