Reaktion #1929016

Reaktionsgleichung

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

Lösungsmittel

ethanol toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe batch is extracted with MTBE
2. 2
   ExtraktionThe aqueous phase is extracted with MTBE
3. 3
   Waschenthe combined organic phases are washed with water
4. 4
   SonstigeThe solution is dried
5. 5
   Einengenconcentrated to dryness
6. 6
   SonstigeThe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1)
7. 7
   SonstigeThe further purification
8. 8
   Sonstigeis carried out by recrystallisation from n-heptane

Vorschrift

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.).

Quelle