Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#N)=[CH:16][CH:15]=1.[N+:22]([O-])([OH:24])=[O:23].CC[O:28]CC>S(=O)(=O)(O)O>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[O:28])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23]
2-bromopyridine (3.3 ml) was dissolved in 30 ml of ether and added with 22.1 ml of butyllithium (1.6 M, in hexane) drop by drop at -30° C. To this mixture were added a solution of 5.0 g of 4-chlorobenzonitrile in ether (10 ml) drop by drop at the same temperature. The reaction mixture was stirred for 1 hour and then poured into ice water. Ether was removed in vacuo. The resultant water-layer fraction was acidified by adding 6 N HCl, stirred at 100° C. for 1 hour, cooled, alkalized by adding sodium hydroxide and then extracted with ether. The resultant ether-layer fraction was concentrated and the oil thus obtained was dissolved in 10 ml of fuming sulfuric acid at 0° C. To this solution, added 1.2 ml of fuming nitric acid drop by drop and the resultant solution was stirred at the same temperature for 1 hour. The reaction mixture was poured into ice water and crystals formed were collected by filtration. The crystals were further recrystallized using ethanol, and 3.6 g of crystalline 2-chloro-5-(2-pyridinecarbonyl)nitrobenzene was thus obtained.
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