Reacción #49788

ord-e3ab984d5c024708ae7185b42301c498

Ecuación de reacción

O=[N+]([O-])c1ccc(Oc2cc(F)c(C(F)(F)F)c(Cl)c2)cc1[N+](=O)[O-]
2-chloro-α,α,α,6-tetrafluoro-p-tolyl 3,4-dinitrophenyl ether
COc1ccc(O)cc1
4methoxyphenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O
water
COc1ccc(Oc2cc(Oc3cc(F)c(C(F)(F)F)c(Cl)c3)ccc2[N+](=O)[O-])cc1
title product
Rendimiento 25.2%
COc1ccc(Oc2cc(Oc3cc(F)c(C(F)(F)F)c(Cl)c3)ccc2[N+](=O)[O-])cc1
4-[(2-Chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]-2-(p-methoxyphenoxy)-1-nitrobenzene
Rendimiento 25.2%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturais refluxed for 18 hours
  2. 2
    Extracciónextracted with ethyl acetate
  3. 3
    ExtracciónThe organic extract
  4. 4
    Lavadois washed with brine
  5. 5
    Secadodried over anhydrous sodium sulfate
  6. 6
    Concentraciónconcentrated in vacuo
  7. 7
    Otroto obtain an amber oil

Procedimiento

A mixture of 2-chloro-α,α,α,6-tetrafluoro-p-tolyl 3,4-dinitrophenyl ether (10.0 g, 0.026 mol), 4methoxyphenol (6.45 g, 0.052 mol) and potassium carbonate (7.26 g, 0.052 mol) in acetonitrile is refluxed for 18 hours, cooled to room temperature, poured into water and extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an amber oil. Column chromatography of the oil using silica gel and a (1:4) ether/hexanes solution gives the title product as a yellow oil (3.0 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05424280uspto-grants-1995_06