Water → 6-Bromo-5-fluoropicolinic Acid

HRID 706575Notes

Reaction equation

HRID 706575 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[OH2:10].[Mn]([O-])(=O)(=O)=[O:12].[K+]>N1C=CC=CC=1>[Br:1][C:2]1[N:3]=[C:4]([C:9]([OH:12])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

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

Product 1

HCID 534011946-Bromo-5-fluoropicolinic AcidYield 17%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

2-Bromo-3-fluoro-6-methylpyridine (3.60 g, 18.9 mmol) was dissolved in 10 mL of pyridine in pressure tube. To this was added 50 mL of water, and the mixture was warmed to 85° C. Potassium permanganate (5.99 g, 37.9 mmol) was added, the tube was capped, and the mixture was stirred at 85° C. for 48 hours. The mixture was filtered through GF/F filter paper, and the filtrate was concentrated to about half volume under reduced pressure. The remaining material was acidified to pH 4 with 1M aqueous HCl and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to give 0.70 g of the title compound (17%).

Workup

  1. customthe tube was capped
  2. filtrationThe mixture was filtered through GF/F
  3. filtrationfilter paper
  4. concentrationthe filtrate was concentrated to about half volume under reduced pressure
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1345d8d8b0b488787e26ad8f1af3f0c
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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