Reaktion #531836

Reaktionsgleichung

4-Bromo-3-fluorophenol

3,5-difluorophenylboronic acid

potassium carbonate

2-propanol

→

4-hydroxy-2,3′,5′-trifluoro-1,1′-biphenyl

Ausbeute 74.0%

Lösungsmittel

Toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for 5 hours under an atmosphere of nitrogen
3. 3
   workup.ADDITIONmixed with it
4. 4
   Sonstigeto separate organic
5. 5
   Extraktionaqueous phases, and extraction
6. 6
   WaschenThe combined organic phase was washed with water
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   EinengenThe resulting solution was concentrated under reduced pressure
9. 9
   Sonstigethe residue was purified with a fractional operation by means of column chromatography (silica gel; toluene)
10. 10
    SonstigeThe product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11
11. 11
    Sonstigedried

Vorschrift

4-Bromo-3-fluorophenol (T-1) (50.0 g), 3,5-difluorophenylboronic acid (45.5 g), potassium carbonate (72.4 g), Pd(Ph3P)2Cl2 (5.52 g) and 2-propanol (500 ml) were put in a reaction vessel and heated to reflux for 5 hours under an atmosphere of nitrogen. After the reaction solution had been cooled to 25° C., it was poured into water (500 ml) and mixed with it. Toluene (500 ml) was added to the solution to separate organic and aqueous phases, and extraction was carried out. The combined organic phase was washed with water and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure and the residue was purified with a fractional operation by means of column chromatography (silica gel; toluene). The product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11 and dried, giving 4-hydroxy-2,3′,5′-trifluoro-1,1′-biphenyl (T-2) (43.4 g). The yield based on the compound (T-1) was 74%.

Quelle