Water → 3,5-Bis-(2-trifluoromethylpyridin-4-yloxy)benzonitrile
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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
- temperaturecooled to room temperature
- customThe phases were separated
- washthe organic phase was washed repeatedly with water and finally with saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8bd2a47560894c11a47af83b98b5e951
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06750222B2
Reaction notes
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