Reacción #1929016

Ecuación de reacción

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

Disolventes

ethanol toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe batch is extracted with MTBE
2. 2
   ExtracciónThe aqueous phase is extracted with MTBE
3. 3
   Lavadothe combined organic phases are washed with water
4. 4
   OtroThe solution is dried
5. 5
   Concentraciónconcentrated to dryness
6. 6
   OtroThe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1)
7. 7
   OtroThe further purification
8. 8
   Otrois carried out by recrystallisation from n-heptane

Procedimiento

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.).

Fuente