Water → 6-Bromo-5-fluoropicolinic Acid

HRID 879093Notes

Reaction equation

HRID 879093 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 (1.0 equiv.) in H2O (30 mL) was added potassium permanganate (1.0 equiv.). The solution was heated at 100° C. for 5 hours at which time more potassium permanganate (1.0 equiv.) 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 pH=4, 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-f3e6fbf7efa74fec8d86f1ba159a9a68
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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