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

HRID 1243372Notes

Reaction equation

HRID 1243372 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 6N 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-05220675543e48c085785f1a56b235bf
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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