Ethanol → 4-Bromo-3-chloroaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-2-chloro-4-nitrobenzene (1.0 g, 4.23 mmol) in THF (7.24 mL) was added EtOH (7.24 mL) followed by ammonium chloride (0.339 g, 6.34 mmol) in water (7.23 mL, 401 mmol) and iron (0.945 g, 16.92 mmol). The reaction mixture was heated at 60° C. in a sealed tube. After 3.5 hours, the reaction mixture was allowed to cool to room temperature and the heterogeneous mixture filtered through a disposable fritted funnel. The filter cake was washed with EtOAc. The solution was concentrated to half-volume, then diluted with EtOAc (10 mL) and 1 N NaOH (10 mL). Layers were separated. Aqueous phase was extracted with EtOAc (3×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford the title compounds as a tan solid. The crude material was used without further purification.

Provenance & Evidence