Stannous Chloride → 3-Bromobenzene-1,2-diamine

A suspension of 2-bromo-6-nitrobenzenamine (2.0 g, 9 mmol) and SnCl2 (10.2 g, 54 mmol) in EtOH (20 mL) was heated at reflux for 2 h, then cooled to RT and concentrated in vacuo. The residue was diluted with EtOAc (100 mL) and washed with saturated NaHCO3 solution (200 mL). The resulting slurry was filtered through a pad of Celite® and washed with EtOAc (50 ml, ×3). The filtrate was washed with saturated NaHCO3, water, and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 3-bromobenzene-1,2-diamine as a brown oil (1.5 g, 90%). MS (ESI): m/z=186.9 [M+1]+.

1. temperaturewas heated
2. temperatureat reflux for 2 h
3. concentrationconcentrated in vacuo
4. additionThe residue was diluted with EtOAc (100 mL)
5. washwashed with saturated NaHCO3 solution (200 mL)
6. filtrationThe resulting slurry was filtered through a pad of Celite®
7. washwashed with EtOAc (50 ml, ×3)
8. washThe filtrate was washed with saturated NaHCO3, water, and brine
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-50415e52d9c643df8d1432bd69692235

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2