反应 #2030723

反应方程式

potassium carbonate

ethanol

toluene

toluene

4-ethoxy-2,3-difluorophenylboronic acid

→

ethyl 4-ethoxy-2,3-difluoro-4′-biphenylbenzoate

溶剂

water

water

反应条件

后处理

1. 1
   其他were put in a reaction vessel under a nitrogen atmosphere
2. 2
   温度heated
3. 3
   温度under reflux for 2 hours
4. 4
   workup.ADDITIONmixed
5. 5
   其他had separated into two phases of organic and
6. 6
   萃取aqueous phases, and extraction into an organic phase
7. 7
   其他The organic phase obtained
8. 8
   洗涤washed with water
9. 9
   干燥dried over anhydrous magnesium sulfate
10. 10
    其他The solution obtained
11. 11
    浓缩was concentrated under reduced pressure
12. 12
    其他the residue obtained
13. 13
    其他was purified with a fractional operation by means of column chromatography
14. 14
    其他The product was further purified by means of recrystallization from ethanol
15. 15
    其他dried

实验过程

4-Iodoethyl benzoate (1) (25.0 g), 4-ethoxy-2,3-difluorophenylboronic acid (2) (20.1 g), potassium carbonate (25.0 g), palladium on carbon (NX type of 5% Pd/C; 50% wet; made by N. E. Chemcat; hereinafter referred to as Pd/C) (0.25 g), toluene (100 ml), ethanol (100 ml) and water (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 2 hours. The reaction mixture was cooled to 25° C., and then poured into water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The product was further purified by means of recrystallization from ethanol and dried, giving 18.8 g of ethyl 4-ethoxy-2,3-difluoro-4′-biphenylbenzoate (3). The yield based on the compound (1) was 67.9%.

来源