Citric Acid → 2-(3-Fluoro-4-nitro-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1678652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678652
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:15])[C:11](Br)([CH3:13])[CH3:12])[CH3:8].[F:16][C:17]1[CH:18]=[C:19]([OH:26])[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.CCOC(C)=O>[CH2:7]([O:9][C:10](=[O:15])[C:11]([O:26][C:19]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([F:16])[CH:18]=1)([CH3:13])[CH3:12])[CH3:8]

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 5209483-Fluoro-4-nitrophenol

Produkt 1

HCID 671311902-(3-Fluoro-4-nitro-phenoxy)-2-methyl-propionic acid ethyl esterAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Potassium carbonate (3.96 g, 29 mmol) and 2-bromo-2-methylpropanoic acid ethyl ester (4.47 g, 23 mmol; CAS Reg. No. 600-00-0) were added to a solution of 3-fluoro-4-nitrophenol (3 g, 19 mmol; CAS Reg. No. 394-41-2) in DMSO (50 ml). The mixture was stirred for 18 h at 100° C. 10% aqueous citric acid and EtOAc were added and the layers were separated. The organic layer was washed with brine and dried over MgSO4. The solid was filtered off and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/heptane) to obtain the title compound (1.19 g, 4.4 mmol; 23%) as yellow oil.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-787e443081614e2d958020cbbc7c29b3
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008505B2

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