Reaction #1929016

Reaction equation

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

Solvents

ethanol toluene

Conditions

Workup

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

Procedure

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