Nitromethane → HCID 22250934, compound

HRID 1255885Notes

Reaction equation

HRID 1255885 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[NH4+].[N+:17]([CH3:20])([O-:19])=[O:18]>>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:20]/[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27348732-Fluoro-4-methoxybenzaldehyde

Product 1

HCID 22250934HCID 22250934, compound

Procedure

A solution of 2-fluoro-4-methoxybenzaldehyde (5.0 g, 33 mmol) and ammonium acetate (1.0 g, 13 mmol) in nitromethane (40 mL) was heated on a steam bath for 2.5 h. The reaction mixture was concentrated under reduced pressure, and the sticky residue was partitioned between CH2Cl2 and H2O. The organic layer was washed with half-saturated brine, dried (MgSO4), filtered, and concentrated. The residue was triturated in hexane and the solid was filtered and washed with hexane and dried to give 2-fluoro-4-methoxy-1-((E)-2-nitrovinyl)benzene (5.57 g) as an orange solid: mp 80-82° C.; 1H NMR (CDCl3): δ 8.02 (d, J=13.5 Hz, 1H), 7.66 (d, J=13.5 Hz, 1H), 7.43 (m, 1H), 6.68-6.80 (m, 2H), 3.87 (s, 3H); EIMS m/z 197 ([M]+). This material was used in the next step without additional purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe sticky residue was partitioned between CH2Cl2 and H2O
  3. washThe organic layer was washed with half-saturated brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated in hexane
  8. filtrationthe solid was filtered
  9. washwashed with hexane
  10. customdried

Sources & evidence

ORD record
ord-522292b5ad6c4320bf6325cf3ad7819f
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

Loading…