Tetrahydrofuran → 4,5-Dichloro-2-methylaniline

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To a partial suspension of 1,2-dichloro-4-methyl-5-nitrobenzene (2.0 g, 9.71 mmol) in MeOH (25 ml), water (25 ml), and THF (10 ml) was added NH4Cl (5.19 g, 97.1 mmol) followed by iron powder (2.71 g, 48.5 mmol). The heterogeneous reaction mixture was heated at 100° C. for 3 h then cooled to room temperature and filtered over a Buchner funnel, rinsing with MeOH. The filtrate was diluted with water and saturated aqueous NaHCO3 then extracted with CH2Cl2 (3×). The combined organics were dried over MgSO4 and concentrated to afford 1.69 g (99%) of 4,5-dichloro-2-methylaniline as a white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.10 (s, 1H), 6.75 (s, 1H), 3.74 (br. s., 2H), 2.12 (s, 3H).

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