Sodium hydride → 2-(3-Bromo-4-nitrophenyl)malonic acid tert-butyl ester methyl ester

HRID 494392

Reaktionsgleichung

[H-].[Na+].[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:15][C:16]1[CH:21]=[C:20](F)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>CN(C)C=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:20]1[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([Br:15])[CH:21]=1)[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Sodium hydride (60%, mineral oil; 0.985 g) was suspended in dimethylformamide (20 mL), and a solution of tert-butyl methyl malonate (4.29 g) in dimethylformamide (5 mL) was added dropwise thereto under ice-cooling. After foam generation is stopped, a solution of 2-bromo-4-fluoro-1-nitrobenzene (2.71 g) in dimethylformamide (5 mL) was added dropwise thereto at the same temperature, and the mixture was further stirred at 60° C. for 3 hours, and then concentrated. The residue was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel with ethyl acetate:hexane=1:4 to 1:5 to give the title compound (7.54 g) as an oil.

Aufarbeitung

temperatureunder ice-cooling
concentrationconcentrated
extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-fd57106f1b3b45019f17b4dfbb54a26f
Quelldatensatz: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07538140B2

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