2-Bromo-1-chloro-4-nitrobenzene → 3-(2-Chloro-5-nitrophenyl)pyridine
Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].B1([C:18]2[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=2)OCCCO1>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1Komponenten
3
Versuchsvorschrift
3-Bromo-4-chloronitrobenzene (5.17 g, 21.9 mmol) was reacted with pyridine-3-boronic acid-1,3-propanediol cyclic ester (4.27 g, 26.2 mmol) over 24 h, as described in Example 62. The resulting crude residue was purified by column chromatography on silica, using 50% diethyl ether in dichloromethane as the eluent, to yield 3-(2-chloro-5-nitrophenyl)pyridine (3.53 g, 69%): δH (360 MHz, CDCl3) 7.42-7.48 (1H, m), 7.70 (1H, d, J 8.7), 7.81 (1H, dt, J 8.0 and 1.8), 8.17-8.27 (2H, m), 8.68-8.77 (2H, m).
Aufarbeitung
- customThe resulting crude residue was purified by column chromatography on silica