Nitric Acid → 3-Chloro-2-(4-chloro-3-nitrophenyl)-5-(trifluoromethyl)pyridine

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Reaction Steps

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.

Provenance & Evidence