[Cl-].[NH4+].O.[I:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[O:14][CH2:15][CH2:16][O:17][CH3:18]>C(O)C.[Fe]>[I:4][C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[O:14][CH2:15][CH2:16][O:17][CH3:18]A suspension of iron (3.89 g, 69.7 mmol), ammonium chloride (5.0 g, 93.5 mmol), in 100 mL of ethanol and 28 mL of water was heated to reflux. 2-Iodo-1-(2-methoxyethoxy)-4-nitrobenzene (7.5 g, 23.2 mmol) was added and the reaction was heated at reflux for 3 hours. The mixture was cooled to room temperature and filtered through Celite, washed with ethanol. The filtrate was concentrated in vacuo until a precipitate appeared. The precipitate was removed by filtration through Magnesol and the filtrate was concentrated in vacuo to provide 4.0 g of [3-iodo-4-(2-methoxyethoxy)phenyl]amine as an oil; 1H NMR (300 MHz, DMSO-d6) δ 3.33 (s, 3H), 3.62 (t, 2H), 3.95 (t, 2H), 5.01 (d, 2H), 6.55 (d, 1H), 6.73 (d, 1H), 7.03 (s, 1H); MS (ES) m/z294.0 (M+H)
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