Hydrochloric Acid → (3-Fluoro-2-nitrophenyl)acetic acid

HRID 2378954Notes

Reaction equation

HRID 2378954 reaction equation
[F:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([CH:8](C(OC)=O)[C:9]([O:11]C)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl>O>[F:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24824212Dimethyl (3-fluoro-2-nitrophenyl)propanedioate

Product 1

HCID 24824213(3-Fluoro-2-nitrophenyl)acetic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl 2-(3-fluoro-2-nitrophenyl)malonate (2.53 g, 9.33 mmol) was suspended in water (20 mL). Concentrated hydrochloric acid (20 ml, 653 mmol) was added to the mixture. Reaction was heated to reflux and held with stirring for 5 hours. Mixture was cooled to room temperature. Material was extracted twice with diethyl ether and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Residue was crystallized from 5:1 hexanes:ethyl acetate. Solids were filtered off, washed with hexanes and then dried in vacuo. Title compound was obtained as white solid in 90% yield. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 3.85 (s, 2 H) 7.08-7.19 (m, 1 H) 7.20-7.28 (m, 1 H) 7.38-7.55 (m, 1 H).

Workup

  1. customReaction
  2. temperaturewas heated
  3. temperatureto reflux
  4. extractionMaterial was extracted twice with diethyl ether
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customResidue was crystallized from 5:1 hexanes
  8. filtrationSolids were filtered off
  9. washwashed with hexanes
  10. customdried in vacuo

Sources & evidence

ORD record
ord-32831e20d04844c7b35d3fe84d4bcd07
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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