Реакция #1929016

Уравнение реакции

1-((Z)-1,2-difluoro-2-iodovinyl)-4-propylcyclohexane

2,3-difluoro-4-ethoxybenzeneboronic acid

sodium carbonate

Water

→

1-[(E)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]-4-ethoxy-2,3-difluorobenzene

Растворители

ethanol toluene

Условия реакции

Обработка

1. 1
   Экстракцияthe batch is extracted with MTBE
2. 2
   ЭкстракцияThe aqueous phase is extracted with MTBE
3. 3
   Промывкаthe combined organic phases are washed with water
4. 4
   ДругоеThe solution is dried
5. 5
   Концентрированиеconcentrated to dryness
6. 6
   ДругоеThe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1)
7. 7
   ДругоеThe further purification
8. 8
   Другоеis carried out by recrystallisation from n-heptane

Методика

6.30 g (20.1 mmol) of 1-((Z)-1,2-difluoro-2-iodovinyl)-4-propylcyclohexane and 4.86 g (24.1 mmol) of 2,3-difluoro-4-ethoxybenzeneboronic acid are refluxed for 19 h together with 1.16 g (1.0 mmol) of tetrakistriphenylpalladium(0) and 20 ml (20 mmol) of sodium carbonate solution (2 M) in 90 ml of ethanol/toluene (2:1). 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. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1). The further purification is carried out by recrystallisation from n-heptane, giving 1-[(E)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]-4-ethoxy-2,3-difluorobenzene as a colourless solid (m.p. 60° C.).

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