반응 #1596951

반응 방정식

4-(4-ethylcyclohexyl)-2-fluorobenzeneboronic acid

hydrazine hydroxide

5-((4-bromo-2,6-difluorophenyl)difluoromethoxy)-1,3-difluoro-2-(trifluoromethyl)benzene

sodium metaborate

→

4-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-4′-(4-ethylcyclohexyl)-3,5,2′-trifluorobiphenyl

용매

water

THF

반응 조건

후처리

1. 1
   기타at room temperature
2. 2
   온도the mixture is heated at the boil for 18 h
3. 3
   온도After cooling
4. 4
   추출the batch is extracted with MTBE
5. 5
   추출The aqueous phase is extracted with MTBE
6. 6
   세척the combined organic phases are washed with water and saturated sodium chloride solution
7. 7
   기타The solution is dried
8. 8
   농축concentrated to dryness
9. 9
   기타The crude product is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=9:1)
10. 10
    기타The further purification
11. 11
    기타is carried out by recrystallisation from ethanol and n-heptane

실험 절차

0.11 ml (2.33 mmol) of hydrazine hydroxide is added to a mixture of 9.70 g (22.1 mmol) of 5-((4-bromo-2,6-difluorophenyl)difluoromethoxy)-1,3-difluoro-2-(trifluoromethyl)benzene, 12 ml (18 mmol) of 1.5 N aqueous sodium metaborate soln. and 0.62 g (0.88 mmol) of bis(triphenylphosphine)palladium(II) chloride in 150 ml of THF at room temperature. 6.1 g (24.3 mmol) of 4-(4-ethylcyclohexyl)-2-fluorobenzeneboronic acid are added, and the mixture is heated at the boil for 18 h. After cooling, water is added, and the batch is extracted with MTBE. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with water and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=9:1). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 4-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-4′-(4-ethylcyclohexyl)-3,5,2′-trifluorobiphenyl as a colourless solid having an m.p. of 77° C.

출처