Nitric Acid → N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

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A mixture of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide (24.4 g, 86.7 mmol) in sulfuric acid is cooled to −3° C., treated dropwise with 70% nitric acid (6.7 mL, 104.0 mmol) while maintaining the temperature from 0° to 2° C., warmed to and stirred at room temperature for 90 minutes, and poured onto ice. The resultant aqueous mixture is filtered to obtain a solid. The solid is washed with water and air-dried overnight to give the title product as a white powder (28.68 g, mp 152-155° C.) which is identified by 1H, 13C and 19F NMR spectral analyses.

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