반응 #531836

반응 방정식

4-Bromo-3-fluorophenol

3,5-difluorophenylboronic acid

potassium carbonate

2-propanol

→

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

수율 74.0%

용매

Toluene

water

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 5 hours under an atmosphere of nitrogen
3. 3
   workup.ADDITIONmixed with it
4. 4
   기타to separate organic
5. 5
   추출aqueous phases, and extraction
6. 6
   세척The combined organic phase was washed with water
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   농축The resulting solution was concentrated under reduced pressure
9. 9
   기타the residue was purified with a fractional operation by means of column chromatography (silica gel; toluene)
10. 10
    기타The product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11
11. 11
    기타dried

실험 절차

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%.

출처