Réaction #1596946

Équation de réaction

2-fluoro-4-(trans-5-propyltetrahydropyran-2-yl)phenyl trifluoromethanesulfonate

2-{4-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolan

sodium carbonate

→

2-{4′-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-2,3′,5′-trifluorobiphenyl-4-yl}-5-propyltetrahydropyran

Solvants

toluene ethanol

Conditions de réaction

Traitement

1. 1
   Températureis heated
2. 2
   Températureunder reflux for 20 h
3. 3
   TempératureAfter cooling
4. 4
   Autrethe organic phase is separated off
5. 5
   Extractionthe aqueous phase is extracted with MTBE
6. 6
   LavageThe combined organic phases are washed with water
7. 7
   AutreThe solution is dried
8. 8
   Concentrationconcentrated to dryness
9. 9
   AutreThe residue is purified by column chromatography (SiO2, n-heptane:toluene=7:3)
10. 10
    AutreThe further purification
11. 11
    Autreis carried out by recrystallisation from ethanol and n-heptane

Mode opératoire

A mixture of 10.0 g (27.0 mmol) of 2-fluoro-4-(trans-5-propyltetrahydropyran-2-yl)phenyl trifluoromethanesulfonate and 14.3 g (29.4 mmol) of 2-{4-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, 1.50 g (1.30 mmol) of tetrakis(triphenylphosphine)palladium(0) and 30 ml of 2 N sodium carbonate solution in 100 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with MTBE. 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:toluene=7:3). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-{4′-[(3,5-difluoro-4-trifluoromethylphenoxy)difluoromethyl]-2,3′,5′-trifluorobiphenyl-4-yl}-5-propyltetrahydropyran as a colourless solid (m.p. 95° C.).

Source