تفاعل #531836

معادلة التفاعل

4-Bromo-3-fluorophenol

3,5-difluorophenylboronic acid

potassium carbonate

2-propanol

→

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

المردود 74.0%

المذيبات

Toluene

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةto reflux for 5 hours under an atmosphere of nitrogen
3. 3
   workup.ADDITIONmixed with it
4. 4
   أخرىto separate organic
5. 5
   استخلاصaqueous phases, and extraction
6. 6
   غسيلThe combined organic phase was washed with water
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   تركيزThe resulting solution was concentrated under reduced pressure
9. 9
   أخرىthe residue was purified with a fractional operation by means of column chromatography (silica gel; toluene)
10. 10
    أخرىThe product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11
11. 11
    أخرىdried

الإجراء التجريبي

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%.

المصدر