Tetrahydrofuran → HCID 66832323, Verbindung
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](Cl)(Cl)=[O:9])=[CH:4][CH:3]=1.[CH:12]([Mg]Br)=[CH2:13].[Cl-].[NH4+].[CH2:18]1COC[CH2:19]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:9])([CH:12]=[CH2:13])[CH:18]=[CH2:19])=[CH:4][CH:3]=1Komponenten
Reaktionsbedingungen
- Temperatur
- -70 °C
Versuchsvorschrift
4-Fluorophenyl-phosphonic dichloride (6.86 g, 32.2 mmol) was dissolved in dry THF (50 mL), placed under a nitrogen atmosphere, and chilled to −70° C. To this stirred solution was added dropwise a solution of vinyl magnesium bromide in THF (80.5 mL, 1M). The resulting solution was stirred for 90 minutes at −70° C. An aqueous solution of ammonium chloride (500 mL, 2M) was chilled to 0° C. and stirred rapidly while the cold reaction mixture was added. The product was extracted into dichloromethane and washed with saturated aqueous sodium bicarbonate followed by water. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 5.214 g of 4-fluoro-phenyl-divinyl-phosphine oxide (26.6 mmol, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) 7.80-7.71 (m, 2H); 7.25-7.18 (m 2H); 6.56-6.22 (m, 6H); ESMS (m/z): (M+1)+ found, 197.
Aufarbeitung
- stirringstirred rapidly while the cold reaction mixture
- additionwas added
- extractionThe product was extracted into dichloromethane
- washwashed with saturated aqueous sodium bicarbonate
- dry with materialThe organic phase was dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
Quellen und Nachweise
- ORD-Eintrag
- ord-d336d5d68b4c4907a03c4ece191ebd93
- Quelldatensatz
- uspto-grants-2011_11
- Patentnummer
- US08067395B2
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