Reacción #157743

ord-dc5ef1fb50724008913e69dd4a136d44

Ecuación de reacción

O
water
FC(F)(F)CI
2,2,2-Trifluoroethyliodide
O=C([O-])[O-].[K+].[K+]
potassium carbonate
Oc1ccc(Br)cc1Cl
4-bromo-2-chlorophenol
FC(F)(F)COc1ccc(Br)cc1Cl
4-bromo-2-chloro-1-(2,2,2-trifluoroethoxy)benzene
Rendimiento 43.0%

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction solution was cooled to room temperature
  2. 2
    Extracciónfollowed by extraction with ethyl acetate
  3. 3
    LavadoThe organic layer was washed with brine
  4. 4
    Secadodried over anhydrous magnesium sulfate
  5. 5
    Filtraciónfiltered
  6. 6
    OtroThe solvent was then evaporated under reduced pressure
  7. 7
    OtroThe residue was purified by silica gel column chromatography (hexane only)

Procedimiento

2,2,2-Trifluoroethyliodide (15.2 g) and potassium carbonate (10.0 g) were added to a solution of 4-bromo-2-chlorophenol (5.0 g) in N,N-dimethylformamide (20 mL), and the mixture was stirred at 80° C. for 20 hours. The reaction solution was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give 4-bromo-2-chloro-1-(2,2,2-trifluoroethoxy)benzene as a colorless oil (3.0 g, 43%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08822503B2uspto-grants-2014_09