تفاعل #1596946

معادلة التفاعل

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

المذيبات

toluene ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis heated
2. 2
   درجة الحرارةunder reflux for 20 h
3. 3
   درجة الحرارةAfter cooling
4. 4
   أخرىthe organic phase is separated off
5. 5
   استخلاصthe aqueous phase is extracted with MTBE
6. 6
   غسيلThe combined organic phases are washed with water
7. 7
   أخرىThe solution is dried
8. 8
   تركيزconcentrated to dryness
9. 9
   أخرىThe residue is purified by column chromatography (SiO2, n-heptane:toluene=7:3)
10. 10
    أخرىThe further purification
11. 11
    أخرىis carried out by recrystallisation from ethanol and n-heptane

الإجراء التجريبي

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.).

المصدر