Nitric Acid → O-ethoxycarbonyl-2,3,4-trifluoro-5-nitrophenol

HRID 1736246Notes

Reaction equation

HRID 1736246 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[C:8]=1[F:15])=[O:5])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[C:10]([F:13])=[C:9]([F:14])[C:8]=1[F:15])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67566268O-ethoxycarbonyl-2,3,4-trifluorophenol

Product 1

HCID 86749656O-ethoxycarbonyl-2,3,4-trifluoro-5-nitrophenolYield 12%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

9.82 g (44.6 mmol) of the above O-ethoxycarbonyl-2,3,4-trifluorophenol was dissolved in 25 mL of concentrated sulfuric acid under ice-cooling, 8.0 mL of fuming nitric acid was added at an internal temperature of 50° C. or below and the mixture was further stirred for 2 hours. The reaction solution was poured into 300 mL of ice water and the mixture was extracted once with ethyl acetate. The organic layer was washed once with water and twice with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to give 1.44 g of O-ethoxycarbonyl-2,3,4-trifluoro-5-nitrophenol (yield: 12%)

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted once with ethyl acetate
  3. washThe organic layer was washed once with water and twice with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-fdc66dcb79694d36b9b6188dc557b41b
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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