반응 #1929011

반응 방정식

1-ethynyl-4-propylcyclohexane

1-bromo-4-ethoxy-2,3-difluorobenzene

→

1-ethoxy-2,3-difluoro-4-(4-propylcyclohexylethynyl)benzene

용매

triethylamine

MTBE

hydrochloric acid

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   기타The organic phase is separated off
3. 3
   추출the aqueous phase is extracted with MTBE
4. 4
   세척The combined organic phases are washed with sodium chloride solution
5. 5
   기타dried
6. 6
   농축The solution is concentrated to dryness
7. 7
   기타the residue is purified by column chromatography (SiO2, n-heptane:chlorobutane=9:1)
8. 8
   기타The further purification
9. 9
   기타is carried out by recrystallisation from n-heptane

실험 절차

A mixture of 20.6 g (0.14 mol) of 1-ethynyl-4-propylcyclohexane, 25.0 g (0.11 mol) of 1-bromo-4-ethoxy-2,3-difluorobenzene, 2.22 g (3.16 mmol) of bis(triphenylphosphine)palladium(II) chloride and 603 mg (3.16 mmol) of copper(I) iodide in 440 ml of triethylamine is warmed at 50° C. for 19 h. After cooling, the mixture is diluted with MTBE and neutralised using dil. hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:chlorobutane=9:1). The further purification is carried out by recrystallisation from n-heptane, giving 1-ethoxy-2,3-difluoro-4-(4-propylcyclohexylethynyl)benzene as a colourless solid (m.p. 64° C.). This has the phase sequence: C 64° C. I. The properties, extrapolated from a 10% solution in ZLI-4792, are:

출처