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

HRID 605956Notes

Reaction equation

HRID 605956 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-8242e3aa083747b7b11e201400c10eef
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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