4'-Fluoroacetophenone → 4'-Fluoro-3'-nitroacetophenone

HRID 581970Notes

Reaction equation

HRID 581970 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=[O:3].[N+:11]([O-])([O-:13])=[O:12].[K+]>S(=O)(=O)(O)O>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 98284'-FluoroacetophenoneHCID 24434Potassium Nitrate

Product 1

HCID 27346124'-Fluoro-3'-nitroacetophenoneYield 60.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

Concentrated sulphuric acid (200 ml) is cooled to 5° C. 4-Fluoroacetophenone (20 ml, 164.76 mmol) is added so that the temperature does not rise above 10° C. The mixture is cooled to 0-5° C. and potassium nitrate (25 g, 247.14 mmol) is added portionwise over 2 hours keeping the temperature at 0-5° C. Following the addition the mixture is stirred at this temperature for 2 hours. The mixture is poured on ice (600 g) and the crude product is filtered off. Column-chromatographic purification on silica-gel using a mixture of ethylacetate and petroleum ether (1:9) as the eluent affords 18.19 g pure 4-fluoro-3-nitroacetophenone (60%).

Workup

  1. customdoes not rise above 10° C
  2. customat 0-5° C
  3. additionthe addition the mixture
  4. additionThe mixture is poured on ice (600 g)
  5. filtrationthe crude product is filtered off
  6. customColumn-chromatographic purification on silica-gel
  7. additiona mixture of ethylacetate and petroleum ether (1:9) as the eluent

Sources & evidence

ORD record
ord-5d207e427a85456db743e105b269170f
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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