1-Bromo-4-nitrobenzene → 5-Bromo-2-nitroaniline

Beteiligte Stoffe

Reaktionsschritte

To a solution of potassium tert-butoxide (14.5 g; 129.2 mmol) and copper(I) chloride (301 mg; 3.04 mmol) in ethyleneglycol dimethylether (120 mL), stirred at 0° C. under nitrogen, a solution of 1-bromo-4-nitro-benzene (1, 6.141 g; 30.4 mmol) and O-methyl-hydroxylamine hydrochloride (3.174 g; 38 mmol) in N,N-dimethylformamide (65 mL) was added drop wise over 103 min, the cooling bath was removed and the mixture was allowed to react at room temperature for 3 h, diluted with ethyl acetate (600 mL) and washed with saturated aqueous ammonium chloride. The organic layer was dried (MgSO4), filtered and concentrated. After purification by flash chromatography (eluent 25% ethyl acetate in hexane), 4.96 g (75% yield) of compound 2 were obtained.

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