反应 #674377

反应方程式

ethyl 2-bromo-4-iodobenzoate

potassium vinyltrifluoroborate

Cs2CO3

triphenylphosphine

→

title compound

Ethyl 2-bromo-4-vinylbenzoate

溶剂

THF water

反应条件

后处理

1. 1
   其他the reaction mixture was degassed with argon for 20 min
2. 2
   温度The reaction mixture was heated
3. 3
   温度to reflux for 16 h
4. 4
   过滤filtered through a Celite® bed
5. 5
   洗涤washed with EtOAc
6. 6
   萃取The filtrate was again extracted with EtOAc
7. 7
   洗涤the combined organic layers washed with water and brine
8. 8
   干燥dried over Na2SO4
9. 9
   浓缩concentrated under reduced pressure
10. 10
    其他to afford crude compound
11. 11
    其他The crude compound was purified by column chromatography (SiO2, 100-200 mesh; eluting with 2% EtOAc/petroleum ether)

实验过程

To a stirred solution of ethyl 2-bromo-4-iodobenzoate (5 g, 14.3 mmol) in THF/water (100 mL, 9:1) was added potassium vinyltrifluoroborate (1.89 g, 14.3 mmol), Cs2CO3 (18.27 g, 56.07 mmol) and triphenylphosphine (0.22 g, 0.85 mmol) and the reaction mixture was degassed with argon for 20 min, then charged with PdCl2 (0.05 g, 0.28 mmol). The reaction mixture was heated to reflux for 16 h. The reaction mixture was cooled to ambient temperature and filtered through a Celite® bed and washed with EtOAc. The filtrate was again extracted with EtOAc and the combined organic layers washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure to afford crude compound. The crude compound was purified by column chromatography (SiO2, 100-200 mesh; eluting with 2% EtOAc/petroleum ether) to afford the title compound as a light brown gummy material (2 g, 56%): 1H NMR (400 MHz, CDCl3) δ 7.78 (d, J=8.4 Hz, 1H), 7.71 (d, J=1.2 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 6.69 (dd, J=17.6, 10.8 Hz, 1H), 5.86 (d, J=17.6 Hz, 1H), 5.42 (d, J=11.2 Hz, 1H), 4.42 (q, J=7.2 Hz, 2H), 1.43 (t, J=3.6 Hz, 3H); ESIMS m/z 255.18 ([M+H]+); IR (thin film) 1729 cm−1.

来源