Nitric Acid → HCID 68986061, compound

HRID 1430470Notes

Reaction equation

HRID 1430470 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 88%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of (2,4-difluoro-phenyl)acetic acid (14.5 g, 0.084 mol) in H2SO4 (60 mL) was treated drop-wise with 69% HNO3 (6 mL), stirred at 0° C. for 35 min, then poured into ice water. The aqueous layer was extracted with EtOAc, and the organic extracts were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography to give (2,4-difluoro-5-nitro-phenyl)acetic acid (16 g, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.30 (t, J=8.0 Hz, 1H), 7.68 (m, 1H), 3.75 (s, 2H).

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. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-1b3f8bacfdbd496a9b9a5282f3d79be3
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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