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

HRID 366554Notes

Reaction equation

HRID 366554 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-4deea6ba24b440229ac725ebf5a895de
Source dataset
uspto-grants-2000_10
Patent number
US06130238

Reaction notes

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