Sodium Sulfate → 2-Bromo-5-(methylsulfonyl)pyridine

HRID 1860599Notes

Reaction equation

HRID 1860599 reaction equation
CS[C:3]1[CH:4]=[CH:5][C:6]([Br:9])=[N:7][CH:8]=1.Cl[C:11]1C=CC=C(C(OO)=O)C=1.[S:21]([O-:25])([O-])(=O)=[O:22].[Na+].[Na+]>C(Cl)Cl>[CH3:11][S:21]([C:3]1[CH:4]=[CH:5][C:6]([Br:9])=[N:7][CH:8]=1)(=[O:25])=[O:22]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acidHCID 116584942-Bromo-5-(methylthio)pyridine

Product 1

HCID 98994832-Bromo-5-(methylsulfonyl)pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methylthio-2-bromopyridine from step 1 (18.9 g, 0.093 mol) in methylene chloride (600 mL), was added portionwise m-chloroperbenzoic acid (48 g, 0.19 mol) at 0° C. and the mixture was stirred for 2 hours at room temperature. Aqueous saturated sodium sulfate (Na2SO3) (200 mL) was added and stirred for 15 minutes and organic phase was separated and washed with aqueous saturated sodium bicarbonate (NaHCO3) (200 mL), dried over MgSO4, and concentrated in vacuo gave the title compound (20.9g, 96%).

Workup

  1. stirringstirred for 15 minutes
  2. customorganic phase was separated
  3. washwashed with aqueous saturated sodium bicarbonate (NaHCO3) (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-334a957861a642f792ee77c19aa58849
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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