Nitric Acid → HCID 68986061, compound

HRID 1930411Notes

Reaction equation

HRID 1930411 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1235812,4-Difluorophenylacetic acid

Product 1

HCID 68986061HCID 68986061, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2,4-difluoro-phenyl)acetic acid (14.5 g, 0.084 mol) in H2SO4 (60 mL) at 0° C. was added dropwise 69% HNO3 (6 mL). After stirring at 0° C. for 35 min, the reaction mixture was poured into ice water. The aqueous layer was extracted with EtOAc, and the organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by chromatography to give (2,4-difluoro-5-nitro-phenyl)acetic acid (16 g, 87.5% yield), 1H NMR (400 MHz, DMSO-d6): δ 8.30 (t, J=8.0 Hz, 1 H), 7.68 (m, 1 H), 3.75 (s, 2 H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-0c014df01ffc46bd88353c8a3c621ae5
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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