反応 #1929016

反応方程式

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

溶媒

ethanol toluene

反応条件

後処理

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

実験手順

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.).

出典