Реакция #1596946

Уравнение реакции

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

Растворители

toluene ethanol

Условия реакции

Обработка

1. 1
   Температураis heated
2. 2
   Температураunder reflux for 20 h
3. 3
   ТемператураAfter cooling
4. 4
   Другоеthe organic phase is separated off
5. 5
   Экстракцияthe aqueous phase is extracted with MTBE
6. 6
   ПромывкаThe combined organic phases are washed with water
7. 7
   ДругоеThe solution is dried
8. 8
   Концентрированиеconcentrated to dryness
9. 9
   ДругоеThe residue is purified by column chromatography (SiO2, n-heptane:toluene=7:3)
10. 10
    ДругоеThe further purification
11. 11
    Другоеis carried out by recrystallisation from ethanol and n-heptane

Методика

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.).

Источник