Nitric Acid → 3-Chloro-2-(4-chloro-3-nitrophenyl)-5-(trifluoromethyl)pyridine
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([N+:1]([O-:4])=[O:2])[CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3.6 g (57 mmol) of concentrated nitric acid were added dropwise to a mixture of 11.1 g (38.0 mmol) of 3-chloro-2-(4-chloro-phenyl)-5-trifluoromethylpyridine in 50 ml of concentrated sulfuric acid while stirring and cooling in ice at 0°-5° C. The mixture was stirred at this temperature for two hours and then poured into 500 ml of ice-water. The product was extracted three times with 150 ml of ethyl acetate each time. The combined organic phases were washed twice with a little water, dried over sodium sulfate and finally concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 95:5). Yield: 11.8 g (90%) of colorless crystals of melting point 68°-69° C.