Dibromodifluoromethane → 4-[2-Fluoro-4-(4'-pentyl-1,1'-bicyclohexane-4-yl)phenyl]difluoromethylenecyclohexane

Temperatur

10 °C

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%.

1. customto react overnight while the reaction mixture
2. customwas coming to room temperature
3. customThe reaction mixture obtained
4. additionmixed
5. customOrganic and aqueous layers were separated
6. additionby adding toluene (300 ml)
7. extractionthe aqueous layer was extracted with toluene
8. washThe organic layers combined were washed sequentially with water, 3N-hydrochloric acid and water
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationThe solution was concentrated under reduced pressure
11. custompurified by means of column chromatography (silica gel; heptane/ethyl acetate)

ORD-Eintrag

ord-ba1be3b5e589496986a265a786a6c0cb

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07951432B2