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

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

1,1,1-trimethylhydrazinium iodide (14.7 g, 72.7 mmol) was added to potassium tert-butoxide (8.20 g, 72.7 mmol) and copper (I) chloride (0.180 g, 1.82 mmol) in DMF (50 mL) at 0° C. The resulting mixture was allowed to stir for several minutes at which point the mixture was cooled to −40° C. and 1-bromo-2,5-dichloro-3-(2-chloro-6-nitrophenoxy)benzene (7.23 g, 18.2 mmol) as a solution in DMF (50 mL) was added dropwise. The reaction mixture was then maintained at −40° C. for 20 minutes, at which point the reaction was quenched at −40° C. with saturated aqueous ammonium chloride (10 mL). Water (10 mL) was then added and the mixture was allowed to warm to room temperature. The mixture was extracted with ethyl acetate (2×200 mL). The combined organic fractions were washed with water (3×200 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by automated column chromatography on silica gel (1.5 kg) eluting with 25% EtOAc/hexanes to give the title compound. LRMS (M+1)=412.4.

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