Iodoethane → 2-Bromo-4-ethoxy-1-(trifluoromethoxy)benzene

HRID 1094821Notes

Reaction equation

HRID 1094821 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[CH2:14](I)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH2:14][CH3:15])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:11])([F:12])[F:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27571943-bromo-4-(trifluoromethoxy)phenol

Product 1

HCID 575823322-Bromo-4-ethoxy-1-(trifluoromethoxy)benzeneYield 125%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the 3-bromo-4-trifluoromethoxyphenol (1.0 g, 2.48 mmol) in acetone (30 ml) was added ethyl iodide (0.795 ml, 9.94 mmol) followed by potassium carbonate (1.37 g, 9.94 mmol) and the reaction was heated to reflux for 12 hrs. The reaction mixture was cooled then filtered and concentrated in vacuo. Dichloromethane (20 ml) and water (20 ml) were added and the solution was filtered through a phase separation cartridge. The organic layer was collected, and evaporated in vacuo to afford crude title compound as a colourless oil (884 mg, 80%). Material was taken on without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 12 hrs
  3. temperatureThe reaction mixture was cooled
  4. filtrationthen filtered
  5. concentrationconcentrated in vacuo
  6. additionDichloromethane (20 ml) and water (20 ml) were added
  7. filtrationthe solution was filtered through a phase separation cartridge
  8. customThe organic layer was collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-20340259bcdd4fb399ce84fc14ed2e5a
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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