Water → 6-Bromo-5-fluoropicolinic Acid

HRID 69940Notes

Reaction equation

HRID 69940 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[Mn]([O-])(=O)(=O)=[O:11].[K+].[OH2:16]>>[Br:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=[O:16])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium Permanganate2×HCID 248203182-Bromo-3-fluoro-6-methylpyridine

Product 1

HCID 534011946-Bromo-5-fluoropicolinic AcidYield 17%

Procedure

To 2-bromo-3-fluoro-6-methylpyridine (2.0 g, 10.58 mmoles) in H2O (30 mL) was added potassium permanganate (1.67 g, 10.58 mmoles). The solution was heated at 100° C. for 5 hours at which time more potassium permanganate (1.67 g, 10.58 mmoles) was added. After heating for an additional 48 hours 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 (200 mL), washed with NaCl(sat.), dried over MgSO4, filtered and concentrated to yield 6-bromo-5-fluoropicolinic acid (17%) as a white solid. LCMS (m/z): 221.9 (MH+); LC Rt=2.05 min.

Workup

  1. additionwas added
  2. temperatureAfter heating for an additional 48 hours the material
  3. filtrationwas filtered through celite (4 cm×2 inches)
  4. washrinsed with H2O (150 mL)
  5. extractionextracted with ethyl acetate (200 mL)
  6. washwashed with NaCl(sat.)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1606300074c543db90ccdbc29980fc31
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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