Acetic Acid → 4-Fluoro-3-nitrophenol

HRID 1976936Notes

Reaction equation

HRID 1976936 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:9])(=O)[CH3:7].CC(C1C=[CH:17][C:16]([F:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=O.C(OO)(=O)C>O>[F:19][C:16]1[CH:17]=[CH:7][C:6]([OH:9])=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 6585Peracetic AcidHCID 27346124'-Fluoro-3'-nitroacetophenone

Product 1

HCID 167518614-Fluoro-3-nitrophenolYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (200 mL) and acetic acid (120) mL are mixed at 0° C. To this solution is added 15 g (0.082 mol) of 4-fluoro-3-nitroacetophenone with stifling. To the cold reaction mixture is added 36 mL of 36% peracetic acid. The reaction mixture is then stirred at room temperature for 4 hours. Water (500 mL) is added to the mixture, and the crude product is extracted into diethyl ether. The combined ether fractions are washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified using column chromatography on silica gel, eluting with 3% methanol/chloroform, giving 3.2 g of Compound 23 (20% yield). mp: 86-87° C. 1H-NMR (CDCl3) 7.56 (dd, 1H); 7.29 (t, 1H), 7.12 (m, 1H); 5.36 (s, 1H). 19F-NMR (d6-DMSO) 147.60 (s). Anal. calc. for C6H4FNO3: C, 45.87; H, 2.57; N, 8.92. Found: C, 45.80; H, 2.51; N, 8.69.

Workup

  1. customTo the cold reaction mixture
  2. extractionthe crude product is extracted into diethyl ether
  3. washThe combined ether fractions are washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified
  8. washeluting with 3% methanol/chloroform

Sources & evidence

ORD record
ord-e36e1b34df614610845e36bc8fa8e81c
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

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