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Water → 3,5-Bis-(2-trifluoromethylpyridin-4-yloxy)benzonitrile

HRID 353205
Notes
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Reaction equation

HRID 353205 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8](F)[CH:9]=1)[C:5]#[N:6].[C:11](=[O:14])([O-])[O-].[K+].[K+].[F:17][C:18]([F:27])([F:26])[C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][N:20]=1.O>CN(C)C(=O)C.C(OCC)(=O)C.CCCCCCC>[F:27][C:18]([F:17])([F:26])[C:19]1[CH:24]=[C:23]([O:25][C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([O:14][C:11]3[CH:22]=[CH:21][N:20]=[C:19]([C:18]([F:27])([F:26])[F:17])[CH:24]=3)[CH:9]=2)[C:5]#[N:6])[CH:22]=[CH:21][N:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5872043,5-DifluorobenzonitrileHCID 178516505HCID 178516505, compound

Product 1

HCID 115609193,5-Bis-(2-trifluoromethylpyridin-4-yloxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 31374
Dimethylacetamide
Solvent
HCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
150 °C

Procedure

Under an atmosphere of nitrogen, 0.556 g (4.0 mmol) of 3,5-difluorobenzonitrile was initially charged in 10 ml of N,N-dimethylacetamide, and 1.22 g (8.8 mmol) of potassium carbonate were added a little at a time at room temperature. 1.305 g (8.00 mmol) of 2-(trifluoromethyl)pyridin-4-ol were then added and the mixture was heated at 150° C. for 30 h and cooled to room temperature, water and ethyl acetate/heptane (1:1) were added to the reaction solution and the solution was stirred for a number of minutes. The phases were separated and the organic phase was washed repeatedly with water and finally with saturated sodium chloride solution and then dried over sodium sulfate, filtered and concentrated. HPLC of the crude product gave 3,5-bis-(2-trifluoromethylpyridin-4-yloxy)benzonitrile in the form of white crystals.

Workup

  1. temperaturecooled to room temperature
  2. customThe phases were separated
  3. washthe organic phase was washed repeatedly with water and finally with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bd2a47560894c11a47af83b98b5e951
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06750222B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes