Acetic Acid → HCID 68724436, compound

Temperature

60 °C

A solution of 1-Chloro-2-nitro-4-((E)-2-nitro-propenyl)-benzene (13.6 g, 56 mmol) in glacial acetic acid (100 ml) is added slowly to a stirred slurry of Iron powder (34 g, 610 mmol) in glacial acetic acid (100 ml) at 60° C. The reaction mixture is stirred at 60° C. for 1 hour then allowed to cool to room temperature and stirred overnight. The reaction mixture is poured onto ice-water (300 ml) and filtered through Celite® (filter agent) washing with DCM (500 ml). The organic portion is separated and washed with water (2×300 ml) and brine (300 ml), dried over MgSO4, filtered and concentrated in vacuo to give a brown oil. The crude residue is absorbed onto silica and purification by flash chromatography on silica eluting with 20% EtOAc/Hexanes affords the title compound.

1. temperatureto cool to room temperature
2. stirringstirred overnight
3. additionThe reaction mixture is poured onto ice-water (300 ml)
4. filtrationfiltered through Celite® (filter agent)
5. washwashing with DCM (500 ml)
6. customThe organic portion is separated
7. washwashed with water (2×300 ml) and brine (300 ml)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give a brown oil
12. customThe crude residue is absorbed onto silica and purification by flash chromatography on silica eluting with 20% EtOAc/Hexanes

ORD record

ord-98bfb31d7fc645f8916e5a652350f29c

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263585B2