Phenol → 4-Chloro-2-phenoxyaniline

HRID 910822

Reaktionsgleichung

Reaktionsgleichung von HRID 910822
F[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([NH2:9])=[C:2]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Produkt 1

HCID 2465634-Chloro-2-phenoxyanilineAusbeute 143,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Fluoro-4-chloro-nitrobenzene (0.50 g), phenol (0.27 g) and potassium carbonate (0.40 g) in dry DMSO (10 ml) were stirred at RT for 2 h. The mixture was diluted with water, extracted with diethylether, dried and evaporated under reduced pressure to give a yellow oil (0.90 g). The oil was dissolved in glacial acetic acid (20 ml) and treated with reduced iron powder (0.90 g). The mixture was vigorously stirred at RT for 2 h, filtered through celite, washed with DCM and the filtrate evaporated under reduced pressure, yield 0.9 g.

Aufarbeitung

  1. extractionextracted with diethylether
  2. customdried
  3. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b410098b22642ddb566b5ebb181f893
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022248B2

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