1-Bromo-2,4-difluoro-5-nitrobenzene → 5-Bromo-2,4-difluoroaniline

Participants

Reaction Steps

To a solution of 1-bromo-2,4-difluoro-5-nitrobenzene (5.04 g, 21.3 mmol) in EtOH (100 mL), THF (50 mL), NH4Cl (sat) (25 mL) and H2O (25 mL) was added iron powder (5.0 g, 89.5 mmol). The mixture was refluxed for 2 h and filtered through celite. The filter pad was washed with EtOAc (3×50 mL). The filtrate was concentrated and the residue was partitioned between EtOAc and brine. The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography (5–10% EtOAc/Hexane) provided 2.6 g (59%) of 5-bromo-2,4-difluoroaniline: ESMS m/e: 208.2 (M+H)+.

Provenance & Evidence