Reaktion #499313

ord-1e462c5bc2744b008f8050aa6339e958

Reaktionsgleichung

CCOC(C)=O
EtOAc
Oc1cccc(OCc2ccccc2)c1
3-(benzyloxy)phenol
O=[N+]([O-])c1cc(Cl)ccc1Cl
2,5-dichloronitrobenzene
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
→
O=[N+]([O-])c1cc(Cl)ccc1-c1cccc(OCc2ccccc2)c1
titled product
O=[N+]([O-])c1cc(Cl)ccc1-c1cccc(OCc2ccccc2)c1
2-[3-(Benzyloxy)phenyl]-5-chloronitrobenzene

Edukte

CCOC(C)=O
EtOAc
Oc1cccc(OCc2ccccc2)c1
3-(benzyloxy)phenol
O=[N+]([O-])c1cc(Cl)ccc1Cl
2,5-dichloronitrobenzene
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate

Reagenzien

Keine

Lösungsmittel

CS(C)=O
DMSO

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooled to room temperature
  2. 2
    Waschenwashed with water, sat. aq. NaHCO3 and brine
  3. 3
    Trocknendried (Na2SO4)
  4. 4
    Filtrationfiltered
  5. 5
    Einengenconcentrated in vacuo

Vorschrift

To a solution of 3-(benzyloxy)phenol (1.145 g, 5.72 mmol) and 2,5-dichloronitrobenzene (1.154 g, 6.01 mmol) in 15 mL of DMSO was added cesium carbonate (3.72 g, 11.4 mmol). The reaction was heated to 70° C. under argon for one hour, then cooled to room temperature. The solution was poured into EtOAc, washed with water, sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The titled product was obtained as a brown oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06562823B1uspto-grants-2003_05