反应 #1929011

反应方程式

1-ethynyl-4-propylcyclohexane

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

→

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

溶剂

triethylamine

MTBE

hydrochloric acid

反应条件

后处理

1. 1
   温度After cooling
2. 2
   其他The organic phase is separated off
3. 3
   萃取the aqueous phase is extracted with MTBE
4. 4
   洗涤The combined organic phases are washed with sodium chloride solution
5. 5
   其他dried
6. 6
   浓缩The solution is concentrated to dryness
7. 7
   其他the residue is purified by column chromatography (SiO2, n-heptane:chlorobutane=9:1)
8. 8
   其他The further purification
9. 9
   其他is carried out by recrystallisation from n-heptane

实验过程

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:

来源