反应 #1596946

反应方程式

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

溶剂

toluene ethanol

反应条件

后处理

1. 1
   温度is heated
2. 2
   温度under reflux for 20 h
3. 3
   温度After cooling
4. 4
   其他the organic phase is separated off
5. 5
   萃取the aqueous phase is extracted with MTBE
6. 6
   洗涤The combined organic phases are washed with water
7. 7
   其他The solution is dried
8. 8
   浓缩concentrated to dryness
9. 9
   其他The residue is purified by column chromatography (SiO2, n-heptane:toluene=7:3)
10. 10
    其他The further purification
11. 11
    其他is carried out by recrystallisation from ethanol and n-heptane

实验过程

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.).

来源