Reacción #1687649

Ecuación de reacción

trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde

tribromofluoromethane

triphenyl phosphine

→

trans-4-(trans-4-ethylcyclohexyl)cyclohexyl-2-fluoro-2-bromoethene

Disolventes

tetrahydrofuran

ethylene glycol dimethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction solution was cooled with ice
2. 2
   Otrowere removed by filtration
3. 3
   workup.ADDITIONDilute hydrochloric acid was added to the filtrate, and it
4. 4
   Extracciónwas extracted with toluene
5. 5
   LavadoAfter the organic layer was washed with water, it
6. 6
   Otrowas dried
7. 7
   Concentraciónconcentrated under a reduced pressure
8. 8
   Otroto obtain a brown oily product
9. 9
   OtroAfter this product was purified
10. 10
    Otrowas recrystallized from heptane

Procedimiento

A solution of tribromofluoromethane and triphenyl phosphine in ethylene glycol dimethyl ether was stirred at 70° C. for 1 hour. The reaction solution was cooled with ice, and a solution of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde in tetrahydrofuran was added thereto. After the reaction solution was further stirred for 1 hour, the temperature of the solution was gradually raised up to room temperature, and insoluble substances were removed by filtration. Dilute hydrochloric acid was added to the filtrate, and it was extracted with toluene. After the organic layer was washed with water, it was dried by using anhydrous magnesium sulfate, and concentrated under a reduced pressure to obtain a brown oily product. After this product was purified by using a silica gel column chromatography, it was recrystallized from heptane to obtain trans-4-(trans-4-ethylcyclohexyl)cyclohexyl-2-fluoro-2-bromoethene.

Fuente