反应 #674374

反应方程式

tert-butyl 2-bromo-4-vinylbenzoate

CuCN

→

title compound

收率 73.9%

tert-Butyl 2-cyano-4-vinylbenzoate

收率 73.9%

溶剂

water

DMF

反应条件

后处理

1. 1
   温度The reaction mixture was cooled to 25° C.
2. 2
   萃取extracted with EtOAc
3. 3
   洗涤The combined organic layer was washed with brine
4. 4
   干燥dried over Na2SO4
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The residue was purified by flash chromatography (SiO2, 100-200 mesh; eluting with 15% EtOAc in n-hexane)

实验过程

To a stirred solution of tert-butyl 2-bromo-4-vinylbenzoate (0.5 g, 1.77 mmol) in DMF (20 mL) was added CuCN (0.23 g, 2.65 mmol), and the reaction mixture was heated at 140° C. for 3 h. The reaction mixture was cooled to 25° C., diluted with water, and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 100-200 mesh; eluting with 15% EtOAc in n-hexane) to afford the title compound as a white solid (0.3 g, 72%): mp 51-53° C.; 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.77 (s, 1H), 7.64 (d, J=8.4 Hz, 1H), 6.75 (dd, J=17.6, 10.8 Hz, 1H), 5.93 (d, J=17.6 Hz, 1H), 5.51 (d, J=10.8 Hz, 1H), 1.65 (s, 9H); ESIMS m/z 229.84 ([M+H]+); IR (thin film) 2370, 1709, 1142 cm−1.

来源