Hydrochloric Acid → Phenyl[2-(trifluoromethyl)-4-nitrophenyl]acetonitrile

HRID 1415581Notes

Reaction equation

HRID 1415581 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[OH-].[Na+].[C:17]1([CH2:23][C:24]#[N:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:24]#[N:25])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 612132-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 54531008Phenyl[2-(trifluoromethyl)-4-nitrophenyl]acetonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 21 parts of 1-chloro-4-nitro-2-(trifluoromethyl)benzene, 180 parts of sodium hydroxide solution 60%, 2parts of N,N,N-triethylbenzenemethanaminium chloride and 90 parts of tetrahydrofuran is added dropwise a mixture of 11.7 parts of benzeneacetonitrile and 27 parts of tetrahydrofuran at 30° C. Upon completion, stirring is continued for 4 hours at 50° C. After cooling, the reaction mixture is poured onto crushed ice. The whole is acidified with a hydrochloric acid solution (pH 1) while the temperature is kept below 20° C. The product is extracted with benzene. The extract is washed with water, dried, filtered and evaporated. The oily residue is crystallized from 70 parts of 2,2'-oxybispropane at 0° C, yielding 4-nitro-α-phenyl-2-(trifluoromethyl) benzeneacetonitrile; mp. 70.4° C.

Workup

  1. additionis added dropwise
  2. temperatureAfter cooling
  3. additionthe reaction mixture is poured
  4. customonto crushed ice
  5. customis kept below 20° C
  6. extractionThe product is extracted with benzene
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe oily residue is crystallized from 70 parts of 2,2'-oxybispropane at 0° C

Sources & evidence

ORD record
ord-8b6afbfd65e84a1f9a761f04c546f1c4
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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