Benzene, 1-iodo-3-(trifluoromethyl)- → 2,2-Difluoro-1-[3-(trifluoromethyl)phenyl]-1-propanone

HRID 339127

Reaktionsgleichung

CC([Mg]Cl)C.I[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[F:17][C:18]([F:26])([CH3:25])[C:19](N(OC)C)=[O:20]>C1COCC1>[F:17][C:18]([F:26])([CH3:25])[C:19]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=[O:20]

Komponenten

Reaktionsbedingungen

Temperatur: -15 °C

Versuchsvorschrift

A solution of 2-propylmagnesium chloride in THF (1.3 M, 7.5 ml) was cooled to −15° C. and admixed with 1-iodo-3-(trifluoromethyl)benzene (2.80 g, 10.2 mmol). The reaction mixture was stirred at −15° C. for 1 h, warmed to room temperature and admixed dropwise with a solution of 2,2-difluoro-N-methoxy-N-methylpropanamide (1.43 g, 9.35 mmol; prepared according to Synth. Comm. 2008 (38), 1940-1945), and stirred at room temperature overnight. Then the mixture was added to ice-cold dilute hydrochloric acid and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 30% EA).

Aufarbeitung

temperaturewarmed to room temperature
stirringstirred at room temperature overnight
additionThen the mixture was added to ice-cold dilute hydrochloric acid
extractionextracted with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% EA to 30% EA)

Quellen und Nachweise

ORD-Eintrag: ord-dcbaa6e30ea6492190224c0783530890
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08889878B2

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