1,2-Dibromoethane → 1-(2-BroMoethoxy)-4(trifluoroMethyl)benzene

HRID 1985282Notes

Reaction equation

HRID 1985282 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O.C(OCC)(=O)C>[Br:12][CH2:13][CH2:14][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenol

Product 1

HCID 146450481-(2-BroMoethoxy)-4(trifluoroMethyl)benzeneYield 21.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5.0 g of 4-hydroxybenzotrifluoride, 17.4 g of 1,2-dibromoethane and 2.6 g potassium carbonate in acetone (100 ml) was heated under reflux for 3 days. The reaction solution was diluted with water and ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated ammonium chloride (×2), dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 1.78 g of the title compound as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated ammonium chloride (×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1bf3eed9062147fbb3c144a31cbaa9f9
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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