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

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)+.

1. temperatureThe mixture was refluxed for 2 h
2. filtrationfiltered through celite
3. washThe filter pad was washed with EtOAc (3×50 mL)
4. concentrationThe filtrate was concentrated
5. customthe residue was partitioned between EtOAc and brine
6. dry with materialThe organic layer was dried over MgSO4
7. concentrationconcentrated
8. customPurification by flash chromatography (5–10% EtOAc/Hexane)

ORD record

ord-0e7abc628b9b4e7d9322d41c78b028ac

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199135B2