Реакция #1929011

Уравнение реакции

1-ethynyl-4-propylcyclohexane

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

→

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

Растворители

triethylamine

MTBE

hydrochloric acid

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling
2. 2
   ДругоеThe organic phase is separated off
3. 3
   Экстракцияthe aqueous phase is extracted with MTBE
4. 4
   ПромывкаThe combined organic phases are washed with sodium chloride solution
5. 5
   Другоеdried
6. 6
   КонцентрированиеThe solution is concentrated to dryness
7. 7
   Другоеthe residue is purified by column chromatography (SiO2, n-heptane:chlorobutane=9:1)
8. 8
   ДругоеThe further purification
9. 9
   Другоеis carried out by recrystallisation from n-heptane

Методика

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:

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