Water → 4'-Methoxy-3'-(trifluoromethyl)acetophenone

HRID 2406029Notes

Reaction equation

HRID 2406029 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][O-:16].[Na+].O>CN(C)C=O>[CH3:15][O:16][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 962WaterHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 27752904'-Methoxy-3'-(trifluoromethyl)acetophenoneYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-fluoro-3′-trifluoromethylacetophenone (25.0 g) in N,N-dimethylformamide (70 ml) was added sodium methoxide (7.21 g) under ice-cooling, and the mixture was stirred for 2 hr under ice-cooling and further at room temperature for 1 hr. The reaction mixture was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (24.3 g) as a brown solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0a21122639dc46cca1066db45c2340b0
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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