Dimethyl 4-fluoro-2-nitrophenylmalonate → 2-(4-Fluoro-2-nitrophenyl)acetic acid

HRID 1937485Notes

Reaction equation

HRID 1937485 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C(OC)=O)[C:9]([O:11]C)=[O:10])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.C(OCC)(=O)C.CCCCCC>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 9838325Dimethyl 4-fluoro-2-nitrophenylmalonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 107504922-(4-Fluoro-2-nitrophenyl)acetic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl 4-fluoro-2-nitrophenylmalonate (5.0 g) was refluxed in 20 mL of 6 N hydrochloric acid for 24 hours. The reaction was cooled and the white solid collected by vacuum filtration, washed with water and dried to give 3.3 g (87% yield) of 4-fluoro-2-nitrophenylacetic acid, Rf 0.6 on thin layer chromatography (ethyl acetate:hexane 1:2, silica gel).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe white solid collected by vacuum filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-19fcbde58ff94ef783388d01adcad080
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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