3-(Trifluoromethyl)phenol → HCID 19087555, compound

HRID 1464244Notes

Reaction equation

HRID 1464244 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.[OH-].[K+].F[C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[C:17]#[N:18]>CN(C)C=O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:15]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:16]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 14797Potassium HydroxideHCID 1235582,5-Difluorobenzonitrile

Product 1

HCID 19087555HCID 19087555, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-trifluoromethylphenol (29 g, 0.18 mol) dissolved in dimethylformamide (100 ml) was added finely-powdered potassium hydroxide (15 g, 0.19 mol). The reaction mixture was heated to approximately 60° C., with stirring, for one hour after which time 2,5-difluorobenzonitrile (25 g, 0.19 mol) was added and the temperature increased to 110° C. After approximately half an hour, the reaction mixture was allowed to cool and excess dimethylformamide was removed in vacuo before 500 ml of a 50:50 mixture of water and trichloromethane was added. The organic layer was separated, washed and dried and the residue purified by chromatography using a silica column with trichloromethane as eluant, followed by distillation and recrystallisation to yield the title compound as a solid.

Workup

  1. additionwas added
  2. temperaturethe temperature increased to 110° C
  3. waitAfter approximately half an hour
  4. temperatureto cool
  5. customexcess dimethylformamide was removed in vacuo before 500 ml of a 50:50 mixture of water and trichloromethane
  6. additionwas added
  7. customThe organic layer was separated
  8. washwashed
  9. customdried
  10. customthe residue purified by chromatography
  11. distillationfollowed by distillation and recrystallisation

Sources & evidence

ORD record
ord-a43c68ed0cac438a9f25ffee12058664
Source dataset
uspto-grants-1994_04
Patent number
US05304532

Reaction notes

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