Tert-Butyl nitrite → HCID 15789986, compound

2-Cyano-6-nitro-4-trifluoromethoxyaniline was converted into 4-chloro-3-cyano-5-nitrotrifluoromethoxybenzene using the general method illustrated in Preparation 5 of EP 0 398 499. In such Preparation, 4-amino-3-chloro-5-cyano-trifluoromethylbenzene (5.1 g) in dry acetonitrile (0.25 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 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.

1. customillustrated in Preparation 5 of EP 0 398 499
2. temperaturewas maintained between 0° and +5° C
3. additionAfter the addition
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with water
6. dry with materialafter drying over anhydrous magnesium sulphate, evaporation of the solvent under reduced pressure
7. customgave an orange oil which
8. customcrystallised
9. distillationKugelrohr distillation

ORD record

ord-913ab3c2ad7f47d5879dd217b6b7fdc6

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05187176