Acetic Acid → 2-(2,6-difluoro-4-nitrophenyl)acetic acid

HRID 2202312Notes

Reaction equation

HRID 2202312 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14].C(O)(=O)C.S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 71283960HCID 71283960, compound

Product 1

HCID 698373442-(2,6-difluoro-4-nitrophenyl)acetic acidYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the obtained diethyl 2,6-difluoro-4-nitrophenylmalonate (42 g) in a mixed solvent of acetic acid (200 mL), water (150 mL) and conc. sulfuric acid (50 mL) was heated under reflux for 18 hr, and the reaction mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate (×2). The organic layer was back-extracted with 10% sodium carbonate aqueous solution, and the aqueous layer was acidified with 2N hydrochloric acid. The precipitate was collected by filtration to give 2-(2,6-difluoro-4-nitrophenyl)acetic acid (27.90 g, 128 mmol, 92.0%) as white crystals.

Workup

  1. temperatureunder reflux for 18 hr
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added water
  4. extractionthe mixture was extracted with ethyl acetate (×2)
  5. extractionThe organic layer was back-extracted with 10% sodium carbonate aqueous solution
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ecf3a3a6cc444de6b820d3910dbe6979
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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