Hydrochloric Acid → 4-methyl-2,3,5,6-tetrafluorobenzonitrile

HRID 1153713Notes

Reaction equation

HRID 1153713 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[C:12]([F:13])=[C:11]([C:14]([NH2:16])=O)[C:10]([F:17])=[C:9]([F:18])[C:8]=1[CH3:19].Cl>C(Cl)Cl.N1C=CC=CC=1>[C:14]([C:11]1[C:10]([F:17])=[C:9]([F:18])[C:8]([CH3:19])=[C:7]([F:6])[C:12]=1[F:13])#[N:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 204362822,3,5,6-Tetrafluoro-4-toluamide

Product 1

HCID 117887354-methyl-2,3,5,6-tetrafluorobenzonitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of phosphorus oxychloride (1.4 g) in methylene chloride (4 ml) was added slowly to a solution of 2,3,5,6-tetrafluoro-4-toluamide (1.0 g) in pyridine (8 ml) at -5° C. When the addition was complete the mixture was warmed to the ambient temperature over a period of 90 minutes, poured into a mixture of dilute hydrochloric acid and ice, and the resultant mixture was extracted with methylene chloride. After washing the extract with water (three times) and drying over anhydrous magnesium sulphate, the solvent was removed by evaporation under reduced pressure. The residual oil was purified by distillation under water pump pressure in a Kugelrohr apparatus to yield 4-cyano-2,3,5,6-tetrafluorotoluene, identified by infra red spectroscopy.

Workup

  1. additionWhen the addition
  2. extractionthe resultant mixture was extracted with methylene chloride
  3. washAfter washing the
  4. extractionextract with water (three times)
  5. dry with materialdrying over anhydrous magnesium sulphate
  6. customthe solvent was removed by evaporation under reduced pressure
  7. distillationThe residual oil was purified by distillation under water

Sources & evidence

ORD record
ord-eccec0ae257c4863a193df954b6def43
Source dataset
uspto-grants-1984_12
Patent number
US04486355

Reaction notes

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