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

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Reaktionsgleichung

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

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

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

Quellen und Nachweise

ORD-Eintrag: ord-9761bf432c7849d0abd1fe14d8c67fd3
Quelldatensatz: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08252826B2

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