Acetic Acid → HCID 15289937, compound

HRID 1975700Notes

Reaction equation

HRID 1975700 reaction equation
C(O)(=[O:3])C.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[C:13]([N+]([O-])=O)[CH2:14][CH3:15]>[Zn].C1(C)C=CC=CC=1>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13](=[O:3])[CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 4226107Benzene, 1-fluoro-2-(2-nitro-1-buten-1-yl)-

Product 1

HCID 15289937HCID 15289937, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

100 ml of 90% v/v aqueous acetic acid were added to 7.4 g of 1-(2-fluorophenyl)-2-nitro-1-butene [prepared as described in step (a) above], and then 12.11 g (190 mmole) of a zinc powder were added in portions to the resulting solution, whilst heating. The mixture was then heated under reflux, whilst stirring, for 4 hours. At the end of this time, the reaction mixture was left to stand overnight, and then the crystals which had precipitated were filtered off and washed with toluene. The filtrate was combined with the toluene washings, and the mixture was concentrated by evaporation under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, using toluene as the eluent, to give 1.85 g of the title compound as a pale brown oil.

Workup

  1. temperaturewhilst heating
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux
  4. waitAt the end of this time, the reaction mixture was left
  5. waitto stand overnight
  6. customthe crystals which had precipitated
  7. filtrationwere filtered off
  8. washwashed with toluene
  9. concentrationthe mixture was concentrated by evaporation under reduced pressure
  10. customThe residue thus obtained

Sources & evidence

ORD record
ord-77ab23f7029045df8a8fefa26e5bce41
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

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