Nitromethane → 2-Fluoro-1-methoxy-4-(2-nitro-vinyl)benzene

HRID 14859

Reaction equation

HRID 14859 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.C([O-])(=O)C.[NH4+].[N+:17]([CH3:20])([O-:19])=[O:18]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:20][N+:17]([O-:19])=[O:18])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 676963-Fluoro-p-anisaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 534146392-Fluoro-1-methoxy-4-(2-nitro-vinyl)benzene

Procedure

3-Fluoro-4-methoxy-benzaldehyde (10 g) was dissolved in 100 mL of nitromethane along with 5 g of ammonium acetate. The mixture was refluxed for 2 hours. The nitromethane was removed by rotary evaporation and the residue recrystallized from ethanol to give 7.6 g of the expected product. LC-MS showed the product had the expected M+H+ of 198.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe nitromethane was removed by rotary evaporation
  3. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-9fee8e75ba3d4258a595d0347fb4ef58
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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