Water → 6-Bromo-3-fluoropyridine-2-carboxylic acid

HRID 69942Notes

Reaction equation

HRID 69942 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:11].[K+].[OH2:16]>>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:11])=[O:16])[C:5]([F:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 27831806-Bromo-3-fluoro-2-methylpyridine

Product 1

HCID 707008736-Bromo-3-fluoropyridine-2-carboxylic acidYield 18%

Conditions

Temperature
100 °C

Procedure

To 6-bromo-3-fluoro-2-methylpyridine (2.0 g, 10.58 mmoles) in H2O (200 mL) was added potassium permanganate (1.67 g, 10.58 mmoles). The solution was heated at 100° C. for 16 hours at which time upon cooling the material was filtered through celite (4 cm×2 inches) and rinsed with H2O (150 mL). The combined aqueous was acidified with 1N HCl to pH4, extracted with ethyl acetate (2×200 mL), washed with NaCl(sat.), dried over MgSO4, filtered and concentrated to yield 6-bromo-3-fluoropicolinic acid (18%) as a white solid. LCMS (m/z): 221.9 (MH+); LC Rt=1.71 min.

Workup

  1. temperatureupon cooling the material
  2. filtrationwas filtered through celite (4 cm×2 inches)
  3. washrinsed with H2O (150 mL)
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washwashed with NaCl(sat.)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ce9e038481b94ba3b031d280762ff856
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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