p-Fluoronitrobenzene → Benzenamine, 2-nitro-4-(4-nitrophenoxy)-

HRID 1294058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294058
[OH:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[H-].[Na+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CN(C=O)C>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([O:1][C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 37588824-Amino-3-Nitrophenol

Produkt 1

HCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-hydroxy-2-nitroaniline (3.08 g, 20.0 mmol) in DMF (30 mL) was added NaH (60% oily, 880 mg, 22.0 mmol) followed by 1-fluoro-4-nitrobenzene (2.33 mL, 22.0 mmol). The mixture was stirred at 90° C. overnight. After cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (4.56 g, 83%): MS m/e 274 (M−1).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthen evaporated
  6. customSequence purification on SiO2 column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c2cbc1d491f14c8788e58d6cdfabb9d5
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238813B2

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