Reaktion #66519

ord-b52fe3e2f3204a35b4cfbbf66d690716

Reaktionsgleichung

O=[N+]([O-])c1ccc(F)c(Cl)c1
2-Chloro-1-fluoro-4-nitrobenzene
Oc1cccc(Cl)c1
3-chlorophenol
O=C([O-])[O-].[Cs+].[Cs+]
Cs2CO3
O=[N+]([O-])c1ccc(Oc2cccc(Cl)c2)c(Cl)c1
2-chloro-1-(3-chlorophenoxy)-4-nitrobenzene
Ausbeute 100.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was quenched with water
  2. 2
    ExtraktionThe aqueous phase was extracted with AcOEt
  3. 3
    WaschenThe organic phase was washed with brine
  4. 4
    Trocknenwas dried over MgSO4
  5. 5
    Filtrationwas filtered
  6. 6
    Einengenwas concentrated under reduced pressure
  7. 7
    SonstigeThe crude product was used without further purification

Vorschrift

According to Scheme 3 Step 1, Method A: 2-Chloro-1-fluoro-4-nitrobenzene (1.12 mmol, 0.20 g) was added to a suspension of 3-chlorophenol (1.02 mmol, 0.10 mL), Cs2CO3 (1.25 mmol, 407 mg) in DMF/ACN (40:60, 3.6 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was used without further purification to obtain 2-chloro-1-(3-chlorophenoxy)-4-nitrobenzene (1.02 mmol, 288 mg, 100%) as an orange solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524726B2uspto-grants-2013_09