Reaktion #90904

Reaktionsgleichung

1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanone

Diethyl [(phenylsulfinyl)methyl]phosphonate

potassium tert-butoxide

→

2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide

Ausbeute 93.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed to room temperature over 30 minutes
2. 2
   workup.ADDITIONThe solution was poured onto hydrochloric acid (3.6%)
3. 3
   Sonstigethe phases were separated
4. 4
   ExtraktionThe aqueous phase was extracted with toluene
5. 5
   Waschenthe combined organic phases were washed with water
6. 6
   Trocknendried over sodium sulfate
7. 7
   Sonstigethe solvents evaporated

Vorschrift

Diethyl [(phenylsulfinyl)methyl]phosphonate (5.00 g, 96% purity, 17.4 mmol) was dissolved in toluene (20 mL) and cooled to 0° C. To the solution potassium tert-butoxide (2.05 g, 18.2 mmol) was added in one portion. This solution was added over 45 minutes to a solution of 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanone (4.26 g, 99% purity, 17.4 mmol) in toluene at 0° C. The reaction mixture was stirred for additional 15 minutes at 0° C. and then warmed to room temperature over 30 minutes. The solution was poured onto hydrochloric acid (3.6%) and the phases were separated. The aqueous phase was extracted with toluene and the combined organic phases were washed with water, dried over sodium sulfate and the solvents evaporated. 2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide was obtained (6.26 g, 94% purity, 93% yield, E/Z=38/62).

Quelle