Iodine → 1,3-difluoro-2-iodo-4-nitrobenzene

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Reaction Conditions

Reaction Steps

A dry, argon-filled Schlenk tube with a magnetic stirrer bar and septum is initially charged with 2,4-difluoro-1-nitrobenzene (159 mg, 1 mmol) in anhydrous THF (2 ml). After adding (TMP)2Zn.MgCl2 (3.00 ml, 1.2 mmol) at 25° C., the mixture is stirred for 30 min, then a solution of iodine (381 mg, 1.5 mmol) in anhydrous THF (2 ml) is added dropwise and the mixture is stirred at 25° C. overnight. For workup, the mixture is diluted with aqueous sat. NH4Cl solution (30 ml) and aqueous sat. Na2S2O3 solution (30 ml) and extracted with ethyl acetate (3×30 ml). After the combined organic phases have been dried over Na2SO4, the solvent has been distilled off and purification has been effected by column chromatography on silica gel (heptane:ethyl acetate), the desired compound (210 mg, 74% of theory) was obtained as a colourless crystalline product.

Provenance & Evidence