Hydrazinium, 1,1,1-trimethyl-, iodide (1:1) → 3-(3-Bromo-5-chlorophenoxy)-4-chloro-2-nitroaniline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To copper (I) chloride (5.45 mg, 0.055 mmol) and potassium tert-butoxide (247 mg, 2.204 mmol) suspended in DMF (3 mL) at 0° C. was added 1,1,1-trimethylhydrazinium iodide (139 mg, 0.689 mmol). This mixture was allowed to stir for several minutes at which point the mixture was cooled to −40° C. and 2-(3-bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene (200 mg, 0.551 mmol) as a solution in DMF (1 mL) was added dropwise. The reaction was maintained at −40° C. for 15 minutes and was then quenched at −40° C. with saturated aqueous ammonium chloride (10 mL). Water (10 mL) was added and the mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with water (3×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by automated column chromatography on silica gel (40 g) eluting with 0-25% EtOAc/hexanes to give the title product. LRMS (M+1)=378.7.

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