Stannous Chloride → 4-Bromo-5-fluoro-1,2-benzenediamine

To a suspension of 96 (1.57 g, 6.74 mmol) in EtOH (16 mL) was added SnCl2 (3.82 g, 20.2 mmol). The reaction mixture was heated at reflux for 14 h, cooled to RT and concentrated in vacuo. The residue was partitioned between EtOAc (100 mL) and sat'd. aq. NaHCO3 (200 mL). The resulting slurry was filtered through a pad of Celite® and the wet cake was washed with EtOAc (3×50 mL). The organic layer was washed sequentially with saturated NaHCO3, water, and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 600 mg (43%) of 4-bromo-5-fluorobenzene-1,2-diamine (98) as yellow solid: MS (ESI) m/z=205 [M+1]+.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 14 h
3. concentrationconcentrated in vacuo
4. customThe residue was partitioned between EtOAc (100 mL)
5. filtrationThe resulting slurry was filtered through a pad of Celite®
6. washthe wet cake was washed with EtOAc (3×50 mL)
7. washThe organic layer was washed sequentially with saturated NaHCO3, water, and brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-7a9c016805e44a2d9e54cc9d32800f67

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2