Hydrochloric Acid → 2-(2,5-Difluoro-4-nitrophenyl)acetic Acid

HRID 2173388Notes

Reaction equation

HRID 2173388 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14].Cl>CC(O)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59163358Diethyl (2,5-difluoro-4-nitrophenyl)propanedioate

Product 1

HCID 675159392-(2,5-Difluoro-4-nitrophenyl)acetic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of diethyl (2,5-difluoro-4-nitrophenyl)propanedioate (700 mg, 2.2 mmol) with HOAc (10 mL) and HCl (6 N, 10 mL) was heated under N2 at 120° C. for 2.5 hours and then allowed to cool and stirred overnight. Most of the solvent was removed by evaporation and then water was added. The mixture was extracted with EtOAc. The organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated to give (2,5-difluoro-4-nitrophenyl)acetic acid.

Workup

  1. temperatureto cool
  2. customMost of the solvent was removed by evaporation
  3. additionwater was added
  4. extractionThe mixture was extracted with EtOAc
  5. washThe organic layer washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2817797d0ad6426b943e0b2ddfe3c8e5
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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