반응 #2487437

반응 방정식

2,2′-azobis(isobutyronitrile)

6-methylnicotinonitrile

N-bromosuccinimide

→

crude material

6-(Bromomethyl)nicotinonitrile

용매

1,2-dichloroethane

반응 조건

후처리

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

실험 절차

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).

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