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

HRID 1502350Notes

Reaction equation

HRID 1502350 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 crystralline 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-cdf8e6fd579d44f6b119adc5b69cc513
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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