Hydrochloric Acid → HCID 15789986, compound

HRID 1089687Notes

Reaction equation

HRID 1089687 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[Cl:14].N(OC(C)(C)C)=O.[ClH:22]>C(#N)C.[Cu](Cl)Cl>[C:8]([C:7]1[CH:6]=[C:5]([C:10]([F:13])([F:12])[F:11])[CH:4]=[C:3]([Cl:14])[C:2]=1[Cl:22])#[N:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 19779379HCID 19779379, compound

Product 1

HCID 15789986HCID 15789986, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

4-Amino-3-chloro-5-cyanotrifluoromethylbenzene (5.1 g) (Preparation 9) in dry acetonitrile (25 ml) was added dropwise to a stirred suspension of copper (II) chloride (3.72 g) and tertiary butyl nitrite (12.24 g) in dry acetonitrile (75 ml) whilst the temperature was maintained between 0° and +5° C. After the addition was complete, stirring was continued for a further 2 hours, whereupon the reaction mixture was diluted with dilute aqueous hydrochloric acid, and extracted with ethylacetate. The organic layer was washed with water, and after drying over anhydrous magnesium sulphate, evaporation of the solvent under reduced pressure gave an orange oil which crystallised on standing. Kugelrohr distillation gave 3-cyano-4,5-dichloro-trifluoromethylbenzene as a pale yellow solid which crystallised on standing.

Workup

  1. temperaturewas maintained between 0° and +5° C
  2. additionAfter the addition
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with water
  5. dry with materialafter drying over anhydrous magnesium sulphate, evaporation of the solvent under reduced pressure
  6. customgave an orange oil which
  7. customcrystallised
  8. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-e486a4c6d9054bad98480c188a9eb0ff
Source dataset
uspto-grants-1992_01
Patent number
US05079251

Reaction notes

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