Hydrochloric Acid → HCID 15789986, compound

HRID 1031124Notes

Reaction equation

HRID 1031124 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-cyano-trifluoromethylbenzene (5.1g) (Preparation 3) in dry acetonitrile (0.25 ml) was added dropwise to a stirred suspension of copper (II) chloride (3.72g) and tertiary butyl nitrite (12.24g) 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 ethyl acetate. 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 oil which crystallised on standing.

Workup

  1. temperaturewas maintained between 0 and +5° C
  2. additionAfter the addition
  3. extractionextracted with ethyl acetate
  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-5edf80340b9743fc928b338f403560ee
Source dataset
uspto-grants-1992_04
Patent number
US05109004

Reaction notes

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