Water → 5-Fluoro-6-(2,3,5-trifluorophenyl)picolinic acid

HRID 1523513Notes

Reaction equation

HRID 1523513 reaction equation
[F:1][C:2]1[C:3]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[C:10]=2[F:17])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Mn]([O-])(=O)(=O)=[O:19].[K+].[OH2:24]>CC(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:19])=[O:24])=[N:4][C:3]=1[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[C:10]=1[F:17]

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 59226524HCID 59226524, compound

Product 1

HCID 592264915-Fluoro-6-(2,3,5-trifluorophenyl)picolinic acidYield 89%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-fluoro-6-methyl-2-(2,3,5-trifluorophenyl)pyridine (1.0 equiv.) in water and t-BuOH (2:1, 0.06 M) was added potassium permanganate (10 equiv.) and the solution was heated at 90° C. for 5 hours. Upon cooling to room temperature, the solution was filtered, and the filtrate was concentrated under reduced pressure to yield 5-fluoro-6-(2,3,5-trifluorophenyl)picolinic acid in 89% yield. LC/MS=272.0 (M+H), Rt=0.80 min.

Workup

  1. temperatureUpon cooling to room temperature
  2. filtrationthe solution was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f527060738484d49a00840f48f803d84
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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