The general procedure for the synthesis of 2-chloro-5-fluoroaniline from 2-chloro-5-fluoronitrobenzene was as follows: a mixture of 0.17 g (1 mmol) of 2-chloro-5-fluoronitrobenzene, 1.13 g (5 mmol) of tin(II) chloride dihydrate, and 10 mL of ethanol was stirred for 0.5 hours at 70 °C. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into 30 mL of water, alkalized with 10% sodium carbonate solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to give 0.12 g (84.5% yield) of the target product 2-chloro-5-fluoroaniline. The structure of the product was confirmed by 1H-NMR (CDCl3, δ): 4.16 (single peak, 2H, NH2), 6.51-6.77 (multiple peaks, 2H, CH on the benzene ring), 7.09-7.21 (multiple peaks, 1H, CH on the benzene ring).
