Reaktion #1596946

Reaktionsgleichung

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

Lösungsmittel

toluene ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated
2. 2
   Temperaturunder reflux for 20 h
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe organic phase is separated off
5. 5
   Extraktionthe aqueous phase is extracted with MTBE
6. 6
   WaschenThe combined organic phases are washed with water
7. 7
   SonstigeThe solution is dried
8. 8
   Einengenconcentrated to dryness
9. 9
   SonstigeThe residue is purified by column chromatography (SiO2, n-heptane:toluene=7:3)
10. 10
    SonstigeThe further purification
11. 11
    Sonstigeis carried out by recrystallisation from ethanol and n-heptane

Vorschrift

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.).

Quelle