3-Chlorophenol → 2-Chloro-1-(3-chlorophenoxy)-4-nitrobenzene

HRID 38241

Reaktionsgleichung

Reaktionsgleichung von HRID 38241
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[Cl:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=1

Komponenten

5

Edukt 3

HCID 79333-ChlorophenolHCID 10796Cesium carbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Produkt 1

HCID 2752072-Chloro-1-(3-chlorophenoxy)-4-nitrobenzeneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21891449acetonitrile N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude product was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b52fe3e2f3204a35b4cfbbf66d690716
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524726B2

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