m-Chloroperbenzoic acid → 4-Bromo-2-methyl-1-oxo-1lambda~5~-pyridine

HRID 1783975Notes

Reaction equation

HRID 1783975 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:17])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:17])=[C:4]([CH3:8])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 544461394-Bromo-2-methyl-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2-methylpyridine (5 g, 29 mmol) in DCM (20 mL) is cooled to 0° C. and m-CPBA (7.55 g, 43.87 mmol, 1.5 equiv.) is added portionwise over 30 min. The ice bath is then removed and the mixture is allowed to stir at room temperature for 3 hours. The resulting solution is diluted with sodium bicarbonate (sat. aq.) and extracted with DCM. The organic layers are combined, washed with sodium bicarbonate (sat. aq.), dried over Na2SO4, and concentrated under vacuum to afford the title compound as a pale orange oil which is without further purification.

Workup

  1. customThe ice bath is then removed
  2. additionThe resulting solution is diluted with sodium bicarbonate (sat. aq.)
  3. extractionextracted with DCM
  4. washwashed with sodium bicarbonate (sat. aq.)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-28eca8fe9b3f4156b195ed7665d89339
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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