Potassium Carbonate → 4-(4-Chloro-3-(trifluoromethyl)phenoxy)benzonitrile

HRID 2359315Notes

Reaction equation

HRID 2359315 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C([O-])([O-])=O.[K+].[K+].F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 805204-Chloro-3-(trifluoromethyl)phenol

Product 1

HCID 580463154-(4-Chloro-3-(trifluoromethyl)phenoxy)benzonitrileYield 105%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)phenol (31.5 g, 160 mmol) in DMSO (200 ml) was added K2CO3 (46.5 g, 337 mmol) at room temperature under nitrogen. After 5 minutes stirring, 4-fluorobenzonitrile (19.4 g, 160 mmol) was added to the mixture in one portion and the resulting mixture was stirred at 100° C. for 18 hours. The reaction mixture was allowed to cool to room temperature and poured into ice-cold 1N aqueous NaOH solution with vigorous stirring. The precipitated solid was collected by filtration and under vacuum to afford 50 g of the title compound.

Workup

  1. stirringthe resulting mixture was stirred at 100° C. for 18 hours
  2. filtrationThe precipitated solid was collected by filtration and under vacuum

Sources & evidence

ORD record
ord-849e242560f74e8ba3c6fb31febb11a2
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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