1094759-93-9

The general procedure for the synthesis of 4-chloro-5-fluoro-2-iodoaniline from 3-fluoro-4-chloroaniline was as follows: iodide iodide (20.6 mL, 1 M dichloromethane solution, 20.6 mmol) was added slowly and dropwise to a solution of 4-chloro-3-fluoroaniline (2 g, 13.7 mmol) in methanol (35 mL) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, volatiles were removed by distillation under reduced pressure, water was added and the mixture was extracted with dichloromethane. The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, and then the solvent was evaporated. The remaining crude product was purified by silica gel column chromatography using three different ratios of eluents in sequence (heptane/ethyl acetate 98:2-93:7, and twice heptane/ethyl acetate 98:2-95:5), resulting in 4-chloro-5-fluoro-2-iodoaniline (2.51 g, 67% yield) as a dark red solid. Mass spectrometry (ESI) analysis showed a molecular ion peak of 272.1 (M + H)+.

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