Hydrochloric Acid → HCID 21483174, compound

HRID 1415580Notes

Reaction equation

HRID 1415580 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+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][CH:19]=1.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[C:25]#[N:26])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 612132-Chloro-5-nitrobenzotrifluorideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 21483174HCID 21483174, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and warmed (30° C) mixture of 105 parts of 1-chloro-4-nitro-2-(trifluoromethyl)benzene, 10 parts of N,N,N-triethylbenzenemethanaminium chloride, 900 parts of sodium hydroxide solution 50% and 135 parts of tetrahydrofuran is added dropwise a mixture of 67.5 parts of 4-fluorobenzeneacetonitrile and 450 parts of tetrahydrofuran (exothermic reaction: temperature rises to 50° C). Upon completion, stirring is continued for 5 hours at 60° C. After cooling, the reaction mixture is poured onto crushed ice and the whole is acidified with a concentrated hydrochloric acid solution, while cooling. The product is extracted with methylbenzene. The extract is washed with water, dried filtered and evaporated. The residue is suspended in a mixture of 2,2'-oxybispropane and petroleumether. The product is filtered off, yielding α-(4-fluorophenyl)-4-nitro-2-(trifluoromethyl)-benzeneacetonitrile; mp. 68° C.

Workup

  1. temperaturewarmed
  2. additionis added dropwise
  3. stirringUpon completion, stirring
  4. temperatureAfter cooling
  5. additionthe reaction mixture is poured
  6. customonto crushed ice
  7. temperaturewhile cooling
  8. extractionThe product is extracted with methylbenzene
  9. washThe extract is washed with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated
  13. additionThe residue is suspended in a mixture of 2,2'-oxybispropane and petroleumether
  14. filtrationThe product is filtered off

Sources & evidence

ORD record
ord-d4902bcdd4c34c82929604f44243aa5b
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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