Ethyl trifluoroacetate → 4,4,4-Trifluoro-2-(4-fluorophenyl)-3-oxobutanenitrile

HRID 2291697Notes

Reaction equation

HRID 2291697 reaction equation
[Na].[F:2][C:3]([F:10])([F:9])[C:4]([O:6]CC)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]#[N:20])=[CH:14][CH:13]=1>C(O)C>[F:10][C:3]([F:2])([F:9])[C:4]([CH:18]([C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=1)[C:19]#[N:20])=[O:6]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 5360545Sodium2×

Product 1

HCID 156138234,4,4-Trifluoro-2-(4-fluorophenyl)-3-oxobutanenitrileYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dry ethanol (15 ml) was added to sodium metal (1.22 g, 0.0530 mole) and the mixture was heated under reflux to dissolve sodium metal perfectly. A mixture of ethyl trifluoroacetate (7.53 g, 0.0530 mole) and p-fluorophenylacetonitrile (6.76 g, 0.0500 mole) was added dropwise over 30 minutes. The mixture, after being heated under reflux for 10 hours, was extracted with methylene chloride to remove neutral and basic components. To the mixture was then added 36% hydrochloric acid to adjust below pH 2 and the mixture was extracted with diethyl ether again. After being dried, the solvent was distilled off under reduced pressure to give the crude title compound (10.47 g, 84.0%). The product showed a single spot on thin-layer chromatography. The product was recrystallized from benzenecyclohexane to recover the monohydrate of the title compound (8.97 g, 77.0%) as pale yellow prisms. The structure of this compound was confirmed by IR and NMR.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. additionwas added dropwise over 30 minutes
  4. temperatureThe mixture, after being heated
  5. temperatureunder reflux for 10 hours
  6. extractionwas extracted with methylene chloride
  7. customto remove neutral
  8. additionTo the mixture was then added 36% hydrochloric acid
  9. extractionthe mixture was extracted with diethyl ether again
  10. customAfter being dried
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ae0b1f40c3284e76930f4e1e81262b87
Source dataset
uspto-grants-1989_01
Patent number
US04797492

Reaction notes

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