Sodium Sulfite → 4-Bromo-2,5-dimethylpyridine 1-oxide

HRID 468832Notes

Reaction equation

HRID 468832 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:9])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:18])C=1.C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-:18])=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 223175304-Bromo-2,5-dimethylpyridine

Product 1

HCID 544438594-Bromo-2,5-dimethylpyridine 1-oxideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2,5-dimethylpyridine (500 mg, 2.69 mmol) was added dropwise to a solution of m-chloroperbenzoic acid (816 mg, 3.55 mmol) in dichloromethane (10 mL) at ambient temperature. The mixture was stirred at room temperature for 17 hours, poured into saturated aqueous sodium bicarbonate and sodium sulfite (2 mL, 1.0M), and extracted twice into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford a yellow crystalline solid (413 mg) which was used without further purification. LCMS: M+H+=202 & 204.

Workup

  1. extractionextracted twice into ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-375773d0794c4619b535595bdabd9c87
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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