4-Bromo-2,6-dinitroaniline → 5-Bromo-3-nitrobenzene-1,2-diamine

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4-bromo-2,6-dinitrobenzenamine was dissolved in EtOH (50 mL) and (NH4)2S (2.2 mL) was added to the mixture. The reaction mixture was heated to 90° C. for 1 h. TLC showed a new compound and some remaining starting material remained. Additionally, another batch (NH4)2S (2.5 mL) was added. After 1 h, TLC analysis showed little starting material remained. The reaction mixture was concentrated to give a deep red solid. It was then purified by silica gel chromatography eluted with DCM to afford the desired product as a red solid (578 mg, 50%). 1H NMR (300 MHz, CDCl3) δ ppm 3.50 (br s, 2H), 5.93 (br s, 2H), 7.04 (d, 1H, J=1.8 Hz), 7.87 (d, 1H, J=1.8 Hz); LC-MS: m/e=232 [M+1]+.

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