Reacción #1596946

Ecuación de reacción

2-fluoro-4-(trans-5-propyltetrahydropyran-2-yl)phenyl trifluoromethanesulfonate

2-{4-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolan

sodium carbonate

→

2-{4′-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-2,3′,5′-trifluorobiphenyl-4-yl}-5-propyltetrahydropyran

Disolventes

toluene ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated
2. 2
   Temperaturaunder reflux for 20 h
3. 3
   TemperaturaAfter cooling
4. 4
   Otrothe organic phase is separated off
5. 5
   Extracciónthe aqueous phase is extracted with MTBE
6. 6
   LavadoThe combined organic phases are washed with water
7. 7
   OtroThe solution is dried
8. 8
   Concentraciónconcentrated to dryness
9. 9
   OtroThe residue is purified by column chromatography (SiO2, n-heptane:toluene=7:3)
10. 10
    OtroThe further purification
11. 11
    Otrois carried out by recrystallisation from ethanol and n-heptane

Procedimiento

A mixture of 10.0 g (27.0 mmol) of 2-fluoro-4-(trans-5-propyltetrahydropyran-2-yl)phenyl trifluoromethanesulfonate and 14.3 g (29.4 mmol) of 2-{4-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, 1.50 g (1.30 mmol) of tetrakis(triphenylphosphine)palladium(0) and 30 ml of 2 N sodium carbonate solution in 100 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:toluene=7:3). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-{4′-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-2,3′,5′-trifluorobiphenyl-4-yl}-5-propyltetrahydropyran as a colourless solid (m.p. 95° C.).

Fuente