3-(Trifluoromethyl)phenol → HCID 22767844, compound

HRID 1606595Notes

Reaction equation

HRID 1606595 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19](Br)[C:20]#[N:21])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH:19]([C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1)[C:20]#[N:21]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 15185681Bromo(4-chlorophenyl)acetonitrile

Product 1

HCID 22767844HCID 22767844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-trifluoromethylphenol (16.2 g., 0.1 mole) and 4-chlorophenyl-α-bromoacetonitrile (23.05 g., 0.1 mole) in methylene chloride (200 ml.) is added potassium carbonate (27.6 g., 0.2 mole). The reaction mixture is stirred and heated under reflux for six hours. The reaction mixture is then cooled to 25°C. and washed with water (300 ml.). The organic layer is dried over sodium sulfate, filtered and the solvent removed to afford crude (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile which is employed in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for six hours
  3. washwashed with water (300 ml.)
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-a5b18ddade784dc59e2533d9514abb86
Source dataset
uspto-grants-1976_04
Patent number
US03953490

Reaction notes

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