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

HRID 474595

Reaction equation

HRID 474595 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>CN(C=O)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

6

Reactant 3

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

Product 1

HCID 580463154-(4-Chloro-3-(trifluoromethyl)phenoxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 4-chloro-3-(trifluoromethyl)phenol (2 g, 10.18 mmol), K2CO3 (2.109 g, 15.26 mmol) and 4-fluorobenzonitrile (1.232 g, 10.18 mmol) in DMF (20 ml), was heated at 120° C. overnight. It was diluted with water and extracted with EtOAc. The organic phases were collected, washed with water and brine, dried over Na2SO4 and concentrated to afford the title compound as a brown oil. LCMS: rt=3.81 min, [M+H+]=298

Workup

  1. extractionextracted with EtOAc
  2. customThe organic phases were collected
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac89e684849b43549bbc219cda80f47c
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Linked notes

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