Water → 4-Chloro-2-(2-trifluoromethylphenyl)butyronitrile

HRID 406358Notes

Reaction equation

HRID 406358 reaction equation
O[CH2:2][CH2:3][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14])[C:5]#[N:6].S(Cl)([Cl:19])=O.O>N1C=CC=CC=1>[Cl:19][CH2:2][CH2:3][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 667786674-Hydroxy-2-(2-trifluoromethylphenyl)butyronitrile

Product 1

HCID 666187134-Chloro-2-(2-trifluoromethylphenyl)butyronitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

4-Hydroxy-2-(2-trifluoromethylphenyl) butyronitrile (2.6 g) was dissolved in pyridine (10 mL). Thionyl chloride (2.1 mL) was carefully added and the mixture was heated with stirring at 60° C. for four hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (1.3 g). The property values of the compound are as follows.

Workup

  1. temperaturethe mixture was heated
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fd5ba77eefc3410a82b2d138e937b0e3
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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