Allyl bromide → 2-[(2-Propenyloxy)-methyl]-5-nitrobenzenamine

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A stirred solution of 2-amino-4-nitrobenzenemethanol (14.3 g, 85 mmol) in dry THF (350 mL) at 0° C. under an argon atmosphere, is treated dropwise over 35 min with a solution of potassium tert-butylate in THF (Fluka; 85 mL of 1.0 M). The mixture is stirred at 0° C. for 15 min and then treated dropwise over 50 min with a solution of allylbromide (7.9 mL, 94 mmol) in dry THF (80 mL) at 0° C. and then stirred at 20° C. for 90 min. The mixture is diluted with ethyl acetate (800 mL). The resulting solution is washed with saturated aqueous ammonium chloride (3×400 mL), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 50% ethyl acetate in hexane, to give the title compound as a brown oil.

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