Reaktion #639213

Reaktionsgleichung

compound ( T-8 )

4-[2-fluoro-4-(4′-pentyl-1,1′-bicyclohexane-4-yl)phenyl]cyclohexanone

Trisdiethylaminophosphine

Dibromodifluoromethane

→

4-[2-fluoro-4-(4′-pentyl-1,1′-bicyclohexane-4-yl)phenyl]difluoromethylenecyclohexane

Ausbeute 84.8%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react overnight while the reaction mixture
2. 2
   Sonstigewas coming to room temperature
3. 3
   SonstigeThe reaction mixture obtained
4. 4
   workup.ADDITIONmixed
5. 5
   SonstigeOrganic and aqueous layers were separated
6. 6
   workup.ADDITIONby adding toluene (300 ml)
7. 7
   Extraktionthe aqueous layer was extracted with toluene
8. 8
   WaschenThe organic layers combined were washed sequentially with water, 3N-hydrochloric acid and water
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    EinengenThe solution was concentrated under reduced pressure
11. 11
    Sonstigepurified by means of column chromatography (silica gel; heptane/ethyl acetate)

Vorschrift

Dibromodifluoromethane (16.2 g) and THF (30 ml) were put into a vessel under a nitrogen atmosphere and cooled to 10° C. Trisdiethylaminophosphine (38.2 g) in THF (50.0 ml) solution was added dropwise thereto and the stirring was continued for another 60 minutes. The compound (T-8) (16.5 g) in THF (400 ml) solution was then added dropwise in the temperature range of 20° C. to 35° C., and allowed to react overnight while the reaction mixture was coming to room temperature. The reaction mixture obtained was poured into ice-water (400 ml) and mixed. Organic and aqueous layers were separated by adding toluene (300 ml) and the aqueous layer was extracted with toluene. The organic layers combined were washed sequentially with water, 3N-hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure and purified by means of column chromatography (silica gel; heptane/ethyl acetate), giving 4-[2-fluoro-4-(4′-pentyl-1,1′-bicyclohexane-4-yl)phenyl]difluoromethylenecyclohexane (T-9) (15.1 g). The yield based on the compound (T-8) was 85%.

Quelle