Stannous Chloride → 3-Bromo-5-fluorobenzene-1,2-diamine

A suspension of 2-bromo-4-fluoro-6-nitroaniline (14 g, 59 mmol) and SnCl2 (66 g, 295 mmol) in EtOH (50 mL) was heated at reflux for 5 h. The reaction mixture was concentrated in vacuo. To the residue was added EtOAc (100 mL) and satd. aq. NaHCO3 (200 mL). The mixture was filtered over Celite® and washed with EtOAc (100 mL×3). The combined organic layers were washed with satd. aq. NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo to afford 3-bromo-5-fluorobenzene-1,2-diamine as a gray solid (10.1 g, 100%). MS (ESI): m/z=205 [M+1]+.

1. temperaturewas heated
2. temperatureat reflux for 5 h
3. concentrationThe reaction mixture was concentrated in vacuo
4. additionTo the residue was added EtOAc (100 mL)
5. filtrationThe mixture was filtered over Celite®
6. washwashed with EtOAc (100 mL×3)
7. washThe combined organic layers were washed with satd
8. dry with materialaq. NaHCO3, water, and brine, dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-736972cb302d4600ad0642949e03928f

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2