2-Bromophenol → 2-(2-bromophenoxy)ethanol

HRID 1582768Notes

Reaction equation

HRID 1582768 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].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][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 111068022-(2-bromophenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a nitrogen atmosphere, 2-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 about 2.5 hours, 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 5.09 g, 81% 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 5.09 g, 81%
  8. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-52e14bb41c64470683a42ed6edebce20
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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