Water → 1-(2-Nitro-vinyl)-4-trifluoromethyl-benzene

HRID 856065Notes

Reaction equation

HRID 856065 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C([O-])(=O)C.[NH4+].O.[N+:19]([CH3:22])([O-:21])=[O:20]>>[N+:19]([CH:22]=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=1)([O-:21])=[O:20]

Participants

5

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 6882311-(2-Nitro-vinyl)-4-trifluoromethyl-benzeneYield 43%

Procedure

4-Trifluoromethylbenzaldehyde (3.00 g, 17.2 mmol) was dissolved in nitromethane (10 ml), to which ammonium acetate (1.341 g, 17.4 mmol) was added, and the mixture was heated under reflux for 2 hours. Water was added to the mixture, which was extracted with methylene chloride twice, and the extracts were combined and washed with brine, and dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1) to afford 1-(2-nitrovinyl)-4-trifluoromethylbenzene (1.596 g, yield 43%) as a pale yellow crystalline powder.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. extractionwas extracted with methylene chloride twice
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-fe3ce31e5205424b8175d840562729bc
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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