4'-Hydroxyacetophenone → 1-[4-(2,2,2-trifluoroethoxy)phenyl]ethanone

HRID 715360Notes

Reaction equation

HRID 715360 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.FC(F)(F)S(O[CH2:17][C:18]([F:21])([F:20])[F:19])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>CN(C=O)C>[F:19][C:18]([F:21])([F:20])[CH2:17][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 74694'-HydroxyacetophenoneHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516892Sodium Bicarbonate

Product 1

HCID 126474971-[4-(2,2,2-trifluoroethoxy)phenyl]ethanoneYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-hydroxyphenyl)ethanone (0.5 g, 3.67 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.58 mL, 4.04 mmol) and cesium carbonate (2.39 g, 7.34 mmol) in DMF (10 mL) is stirred at rt for 2.5 hours. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate (10 mL) and extracted with EtOAc (30 mL). The organic layer is washed with saturated aqueous sodium hydrogen carbonate (10 mL×2) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo to give 0.65 g (81% yield) of the title compound as white solid. This material is used for the next reaction (Step-2) without further purification.

Workup

  1. extractionextracted with EtOAc (30 mL)
  2. washThe organic layer is washed with saturated aqueous sodium hydrogen carbonate (10 mL×2)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-2520c037169249c8a8fcd58bed7cd455
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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