1-Chloro-2-iodo-3-nitrobenzene → 3-Chloro-2-iodoaniline

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To a stirred solution of 1-chloro-2-iodo-3-nitrobenzene (143-2; 1.4 g, 0.00490 mol) in ethanol (20 mL) was added stannous chloride dihydrate (5.5 g, 0.0245 mol) portion wise at 0° C. Reaction mixture was allowed to stir at 70° C. for 30 min. The reaction mixture was concentrated and diluted with ice cold water (150 mL) and PH was made slightly basic by addition of saturated aqueous sodium carbonate solution before being extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.048-7.008 (t, 8 Hz, 1H), 6.713-6.693 (dd, J=8, 8.8 Hz, 1H), 6.655-6.632 (dd, J=8.4, 9.2 Hz, 1H), 5.5 (bs, 2H).

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