反应 #1929016

反应方程式

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

溶剂

ethanol toluene

反应条件

后处理

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

实验过程

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.).

来源