Nitric Acid → 4'-Fluoro-3'-nitroacetophenone

HRID 1976935Notes

Reaction equation

HRID 1976935 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8].[N+:16]([O-])([OH:18])=[O:17]>>[CH3:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)=[O:8]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 98284'-Fluoroacetophenone

Product 1

HCID 27346124'-Fluoro-3'-nitroacetophenoneYield 60%

Conditions

Temperature
2.5 °C

Procedure

To 15 mL of concentrated sulfuric acid at 0° C. is added 6.9 g (0.05 mmol) of 4-fluoroacetophenone. To the resulting solution is rapidly added a mixture of 4 mL nitric acid and 6 mL concentrated sulfuric acid. The reaction mixture is stirred at 0-5° C. for 3 hours. The reaction mixture is then poured into ice water, and the resulting mixture is extracted with chloroform. The combined organic fractions are washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified using column chromatography on silica gel, eluting with 20% ethyl acetate/hexanes, yielding 6.0 g of 4-fluoro-3-nitroacetophenone (60% yield).

Workup

  1. additionTo the resulting solution is rapidly added
  2. extractionthe resulting mixture is extracted with chloroform
  3. washThe combined organic fractions are washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified
  8. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a457abd543074aa19a18b8dde53cce67
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

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