4-Fluorophenol → 3-(4-Fluorophenoxy)aniline

HRID 29881

Reaktionsgleichung

Reaktionsgleichung von HRID 29881
F[C:2]1[CH:3]=[C:4]([N+:8]([O-])=O)[CH:5]=[CH:6][CH:7]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CNC>[F:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 97324-FluorophenolHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium Carbonate

Produkt 1

HCID 235060153-(4-Fluorophenoxy)anilineAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 674DimethylamineLösungsmittel

Versuchsvorschrift

Alternatively, 3-(4-fluoro-phenoxy)-phenylamine was prepared by a two-step procedure by heating a suspension of m-fluoronitrobenzene (4.06 g, 28.7 mmol), p-fluorophenol (3.21 g, 28.6 mmol) and K2CO3 (8.13 g, 58.8 mmol) in DMA (dimethylamine) (60 mL) at 150° C. for 3 hours. The brown reaction mixture was concentrated to one-quarter original volume, diluted with ethyl acetate (220 mL) and washed successively with water (220 mL), 1N NaOH (220 mL) and brine (220 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford the diphenylether (5.30 g, 80%) as a brown oil.

Aufarbeitung

  1. customAlternatively, 3-(4-fluoro-phenoxy)-phenylamine was prepared by a two-step procedure
  2. temperatureby heating
  3. concentrationThe brown reaction mixture was concentrated to one-quarter original volume
  4. additiondiluted with ethyl acetate (220 mL)
  5. washwashed successively with water (220 mL), 1N NaOH (220 mL) and brine (220 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b2c63fa300748dea9d913c55c851a3d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423043B2

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