Potassium Permanganate → 5-Bromo-4-chloropyridine-2-carboxylic acid

HRID 2196408Notes

Reaction equation

HRID 2196408 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[Br:7][C:8]1[C:9]([Cl:16])=[CH:10][C:11]([CH2:14][OH:15])=[N:12][CH:13]=1>O.C([O-])([O-])=O.[Na+].[Na+]>[Br:7][C:8]1[C:9]([Cl:16])=[CH:10][C:11]([C:14]([OH:1])=[O:15])=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 19791171(5-Bromo-4-chloropyridin-2-yl)methanol

Product 1

HCID 583866545-Bromo-4-chloropyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

KMnO4 (174 mg, 1.1 mmol) in H2O was added dropwise to a solution of (5-bromo-4-chloro-2-pyridinyl)methanol (187 mg, 0.846 mmol) in 10% Na2CO3 (1 mL). After 2 h, the solution was filtered through Celite®, adjusted to pH ˜4 and the resulting precipitate was filtered then azeotropically dried with toluene affording the title compound (135 mg, 68%) as a white powder: LCMS (ES) m/z=237 (M+H)+.

Workup

  1. filtrationthe solution was filtered through Celite®
  2. filtrationthe resulting precipitate was filtered
  3. dry with materialthen azeotropically dried with toluene affording the title compound (135 mg, 68%) as a white powder

Sources & evidence

ORD record
ord-608892ddeed049afa11b1803466c8a98
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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