反应 #674378

反应方程式

ethyl 2-chloro-4-bromobenzoate

potassium vinyltrifluoroborate

K2CO3

→

material

收率 69.0%

Ethyl 2-chloro-4-vinylbenzoate

收率 69.0%

溶剂

water

DMSO

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   萃取extracted with EtOAc (2×50 mL)
3. 3
   洗涤washed with brine
4. 4
   干燥dried over Na2SO4
5. 5
   浓缩concentrated under reduced pressure

实验过程

To a stirred solution of ethyl 2-chloro-4-bromobenzoate (2 g, 7.63 mmol) in DMSO (20 mL) was added potassium vinyltrifluoroborate (3.06 g, 22.9 mmol) and K2CO3 (3.16 g, 22.9 mmol). The reaction mixture was degassed with argon for 30 min Bistriphenylphosphine(diphenylphosphinoferrocene)palladium dichloride (0.27 g, 0.38 mmol) was added and the reaction mixture was heated to 80° C. for 1 h. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (2×50 mL), washed with brine, dried over Na2SO4 and concentrated under reduced pressure to obtain the compound as brown gummy material (1.1 g, 69%): 1H NMR (400 MHz, CDCl3) δ 7.81 (d, J=8.4 Hz, 1H), 7.46 (s, 1H), 7.33 (d, J=8.4 Hz, 1H), 6.70 (dd, J=17.6, 11.2 Hz, 1H), 5.87 (d, J=17.6 Hz, 1H), 5.42 (d, J=10.8 Hz, 1H), 4.41 (q, J=7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H); ESIMS m/z 211.22 ([M+H]+); IR (thin film) 1729, 886 cm−1.

来源