4-Fluorophenol → Methyl 3-(4-fluorophenoxy)-5-nitrobenzoate

HRID 523950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 523950
[N+]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:4]2[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 97324-FluorophenolHCID 62657Potassium Phosphate, TribasicHCID 222067Methyl 3,5-dinitrobenzoate

Produkt 1

HCID 86730099Methyl 3-(4-fluorophenoxy)-5-nitrobenzoateAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The compound prepared in Example 34 (4.73 g) was dissolved in DMF (40 mL), added with 4-fluorophenol (2.34 g) and potassium phosphate (5.32 g) and stirred overnight at 80° C. The reaction solution was diluted with ethyl acetate, sequentially washed with water and a saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1→1:1) to give the titled compound (4.81 g) having the following physical properties.

Aufarbeitung

  1. washsequentially washed with water
  2. dry with materiala saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent
  3. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ca959dc561a3471f861f3ba93397f35d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340499B2

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