Isopropanol → 5-Bromo-4-chloropyridine-2-carboxylic acid

HRID 74597Notes

Reaction equation

HRID 74597 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[Mn]([O-])(=O)(=O)=[O:12].[K+].C(O)(C)C>CC(C)=O.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[C:3]([Cl:10])=[CH:4][C:5]([C:8]([OH:12])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 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 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent2×

Procedure

0.50 g (2.3 mmol) (5-bromo-4-chloro-pyridin-2-yl)-methanol in 8 mL acetone were added dropwise at RT to 0.71 g (4.5 mmol) potassium permanganate in 10 mL acetone and then the mixture was stirred for 17 h at RT. Then 10 mL isopropanol were added and the mixture was stirred for a further 5 h at RT. The precipitated manganese dioxide was suction filtered and washed with water. The filtrate was partially evaporated down and the aqueous phase was adjusted to a pH of 3 with 1N aqueous hydrochloric acid solution. The precipitate formed was suction filtered.

Workup

  1. stirringthe mixture was stirred for a further 5 h at RT
  2. filtrationfiltered
  3. washwashed with water
  4. customThe filtrate was partially evaporated down
  5. customThe precipitate formed
  6. filtrationfiltered

Sources & evidence

ORD record
ord-91c6785124194a5c8e989cd70cb022a9
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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