Réaction #1929016

Équation de réaction

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

Solvants

ethanol toluene

Conditions de réaction

Traitement

1. 1
   Extractionthe batch is extracted with MTBE
2. 2
   ExtractionThe aqueous phase is extracted with MTBE
3. 3
   Lavagethe combined organic phases are washed with water
4. 4
   AutreThe solution is dried
5. 5
   Concentrationconcentrated to dryness
6. 6
   AutreThe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1)
7. 7
   AutreThe further purification
8. 8
   Autreis carried out by recrystallisation from n-heptane

Mode opératoire

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.).

Source