Nitromethane → HCID 22250934, compound

HRID 1467407Notes

Reaction equation

HRID 1467407 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 dichloromethane and water. 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 5.57 g of crude product 2-fluoro-4-methoxy-1-((E)-2-nitrovinyl)benzene as an orange solid, M.P. 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). GC/MS: 197 [M]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe sticky residue was partitioned between dichloromethane and water
  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-9d13988d00e847f395f99863c5b873a9
Source dataset
uspto-grants-2015_04
Patent number
US09000162B2

Reaction notes

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