反応 #531836

反応方程式

4-Bromo-3-fluorophenol

3,5-difluorophenylboronic acid

potassium carbonate

2-propanol

→

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

収率 74.0%

溶媒

Toluene

water

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to reflux for 5 hours under an atmosphere of nitrogen
3. 3
   workup.ADDITIONmixed with it
4. 4
   その他to separate organic
5. 5
   抽出aqueous phases, and extraction
6. 6
   洗浄The combined organic phase was washed with water
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   濃縮The resulting solution was concentrated under reduced pressure
9. 9
   その他the residue was purified with a fractional operation by means of column chromatography (silica gel; toluene)
10. 10
    その他The product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11
11. 11
    その他dried

実験手順

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%.

出典