3-(Trifluoromethyl)phenol → HCID 86666204, compound

HRID 474625Notes

Reaction equation

HRID 474625 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:21])[F:22])[CH:15]=1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 86666204HCID 86666204, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-fluoro-3-(methyloxy)benzaldehyde (1.07 g, 6.94 mmol) and 3-(trifluoromethyl)phenol (1.238 g, 7.64 mmol) in DMF (25 mL) was added K2CO3 (2.88 g, 20.83 mmol) under argon. The mixture was heated at 90° C. for 0.5 h. After removing the solvent, the residue was diluted with water, extracted with DCM. The organic phase was dried over sodium sulfate, filtered, and concentrated to afford the title compound (1.735 g, 5.86 mmol, 84% yield). LCMS: rt=3.53 min, [M+H+]=297

Workup

  1. customAfter removing the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b7ad99da5c2d4f2ea2a74e575294b778
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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