5-Bromo-2-(methylthio)pyridine → 5-Bromo-2-methanesulfonylpyridine

HRID 496806Notes

Reaction equation

HRID 496806 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[OH2:10].[OH2:11].O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2]>ClCCl.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH3:9])(=[O:11])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 114242515-Bromo-2-(methylthio)pyridineHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 134334245-Bromo-2-methanesulfonylpyridineYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-bromo-2-methylsulfanyl pyridine (3.47 g) was dissolved in a mixed solvent of dichloromethane and methanol with the ratio of 5:1 (v/v) and magnesium monoperoxyphthalate hexahydrate was slowly added dropwise. After completing the reaction for 3 hours at room temperature, magnesium monoperoxyphthalate hexahydrate was filtered out, sodium bicarbonate and salt water was added to dilute, and extracted with dichloromethane to separate an organic layer. The separated organic layer was dried with anhydrous magnesium sulfate and distilled under reduced pressure. As a result, 5-bromo-2-methylsulfonyl pyridine (3.7 g, yield: 92%) was obtained as a white solid.

Workup

  1. additionwas slowly added dropwise
  2. customthe reaction for 3 hours at room temperature
  3. filtrationmagnesium monoperoxyphthalate hexahydrate was filtered out
  4. additionsodium bicarbonate and salt water was added
  5. additionto dilute
  6. extractionextracted with dichloromethane
  7. customto separate an organic layer
  8. dry with materialThe separated organic layer was dried with anhydrous magnesium sulfate
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-df17a300a0d6499e9f3c2d8eac9914c3
Source dataset
uspto-grants-2005_09
Patent number
US06946558B2

Reaction notes

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