2-Bromo-4-nitroanisole → 3-Bromo-4-methoxyaniline

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Stannous chloride (96.839 g, 5.0 eq.) was added to a solution of 2-bromo-4-nitroanisole (23.7 g, 1.0 eq.) in ethanol (250 mL) and the mixture was stirred at 70° C. for 2 h, partitioned between ethyl acetate and sodium bicarbonate solution 10%. The pH was adjusted to 9 with 1N sodium hydroxide solution and the aqueous layer was extracted twice with ethyl acetate. The combined organic fractions were washed with water and brine, dried over magnesium sulfate, filtered, evaporated to dryness and purified on silica gel, eluting with hexane/ethyl acetate 1:1, to yield 13.82 g (67%) from the desired product as light brown solid. MS (m/e): 204.1 (MH+, 100%).

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