反应 #2487437

反应方程式

2,2′-azobis(isobutyronitrile)

6-methylnicotinonitrile

N-bromosuccinimide

→

crude material

6-(Bromomethyl)nicotinonitrile

溶剂

1,2-dichloroethane

反应条件

后处理

1. 1
   其他After complete consumption of the starting material (by TLC)
2. 2
   温度the reaction mixture was cooled to RT
3. 3
   其他the volatiles were removed under reduced pressure

实验过程

To a stirred solution of 6-methylnicotinonitrile (1.0 g, 8.47 mmol) in 1,2-dichloroethane (30 mL) was added N-bromosuccinimide (NBS; 1.52 g, 8.54 mmol) and followed by 2,2′-azobis(isobutyronitrile) (AIBN; 0.14 g, 0.85 mmol) at RT. The reaction mixture was then heated to 80° C. and stirred for 14 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT, and the volatiles were removed under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 10% EtOAc/Hexane) afforded compound I-4 (0.6 g, 3.05 mmol, 36%) as a colorless liquid. 1H NMR (500 MHz, CDCl3): δ 7.67-7.62 (m, 2H), 7.21 (dd, J=9.0, 2.0 Hz, 1H), 4.44 (s, 2H).

来源