2,6-Dibromo-4-nitroaniline → 1,3-dibromo-5-nitrobenzene

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Reaction Steps

NaNO2 (4.1 g, 59.1 mmol) was added portionwise to a solution of 2,6-dibromo-4-nitroaniline (5 g, 3.5 eq) in 20% H2SO4 and AcOEt (each 40 mL) at a rate to keep the internal temperature at 50-55° C. After heating for an additional 10 min, the mixture was cooled, diluted, and extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (cyclohexane/DCM//7/3 then 8/2) to yield expected compound as a white solid (1.94 g, 41% yield).

Provenance & Evidence