反应 #674379

反应方程式

ethyl 2-methyl-4-vinylbenzoate

1-(1-bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene

2,2bipyridyl

→

title compound

收率 40.0%

(E)-Ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoate

收率 40.0%

溶剂

1,2-dichlorobenzene

反应条件

后处理

1. 1
   其他The reaction mixture was degassed with argon for 30 min
2. 2
   温度the reaction mixture was cooled to 25° C.
3. 3
   过滤filtered
4. 4
   浓缩the filtrate was concentrated under reduced pressure
5. 5
   其他Purification
6. 6
   洗涤by flash chromatography (SiO2, 100-200 mesh; eluting with 25-30% EtOAc in petroleum ether)

实验过程

To a stirred solution of ethyl 2-methyl-4-vinylbenzoate (2.0 g, 10.5 mmol) in 1,2-dichlorobenzene (25 mL) were added 1-(1-bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene (6.44 g, 21.0 mmol), CuCl (208 mg, 21 mmol) and 2,2bipyridyl (0.65 g, 4.1 mmol). The reaction mixture was degassed with argon for 30 min and then stirred at 180° C. for 24 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to 25° C. and filtered, and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; eluting with 25-30% EtOAc in petroleum ether) afforded the title compound as a solid (1.7 g, 40%): 1H NMR (400 MHz, CDCl3) δ 7.91 (d, J=8.0 Hz, 1H), 7.37 (m, 1H), 7.27-7.24 (m, 4H), 6.59 (d, J=16.0 Hz, 1H), 6.59 (dd, J=16.0, 8.0 Hz, 1H), 4.38 (q, J=7.2 Hz, 2H), 4.08 (m, 1H), 2.62 (s, 3H), 1.42 (t, J=7.2 Hz, 3H); ESIMS m/z 415.06 ([M−H]−); IR (thin film) 1717, 1255, 1114 cm−1.

来源