反応 #1929011

反応方程式

1-ethynyl-4-propylcyclohexane

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

→

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

溶媒

triethylamine

MTBE

hydrochloric acid

反応条件

後処理

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

実験手順

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:

出典