Dimethyl (3-fluoro-2-nitrophenyl)propanedioate → (3-Fluoro-2-nitrophenyl)acetic acid

HRID 2250516Notes

Reaction equation

HRID 2250516 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[N+:16]([O-:18])=[O:17])C(OC)=O>Cl.O>[F:15][C:11]1[C:10]([N+:16]([O-:18])=[O:17])=[C:9]([CH2:4][C:3]([OH:19])=[O:2])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 24824212Dimethyl (3-fluoro-2-nitrophenyl)propanedioate

Product 1

HCID 24824213(3-Fluoro-2-nitrophenyl)acetic acidYield 86.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

2-(3-Fluoro-2-nitro-phenyl)-malonic acid dimethyl ester (12 g, 44 mmol) in 200 mL 6N hydrochloric acid (6N, 200 mL) was heated under reflux for 4 hours. The mixture was cooled, diluted with 250 mL of water and extracted with diethyl ether, dried (MgSO4), and concentrated in vacu., Crystallization from hexane/ethylacetate (95/5), gave (3-fluoro-2-nitro-phenyl)-acetic acid (7.6 g, 54%) which was used without further examination.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethyl ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacu
  6. custom, Crystallization from hexane/ethylacetate (95/5)

Sources & evidence

ORD record
ord-4a8acb9beebe44c4bc99c6b58f049822
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

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