Ethanol → 4-Bromo-3-chloroaniline

Temperature

60 °C

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.

1. temperatureto cool to room temperature
2. filtrationthe heterogeneous mixture filtered through a disposable fritted funnel
3. washThe filter cake was washed with EtOAc
4. concentrationThe solution was concentrated to half-volume
5. additiondiluted with EtOAc (10 mL) and 1 N NaOH (10 mL)
6. customLayers were separated
7. extractionAqueous phase was extracted with EtOAc (3×)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-fc0d1f2baafb437caad1c82700e081fa

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916553B2