m-Chloroperbenzoic acid → 3-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate

HRID 2390862

Reaction equation

HRID 2390862 reaction equation
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:9])=[N+:4]([O-:18])[C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27344183-Bromo-2-chloro-6-methylpyridine

Product 1

HCID 857064893-Bromo-2-chloro-6-methylpyridin-1-ium-1-olateYield 1,230.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

step a—To a solution of 3-bromo-2-chloro-6-methyl-pyridine (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50° C. overnight. The resulted solution was cooled and partitioned between DCM and sat'd. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of 3-bromo-2-chloro-6-methyl-pyridine 1-oxide (357a) as a white solid.

Workup

  1. temperatureThe resulted solution was cooled
  2. custompartitioned between DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with an EtOAc/hexane gradient (30 to 80% EtOAc)

Sources & evidence

ORD record
ord-018b7ca9aaaf4f3b845ebada39f7db3d
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Linked notes

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