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

HRID 1634283Notes

Reaction equation

HRID 1634283 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.[O-:21][S:22]([O-:24])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:11][S:22]([C:3]1[CH:4]=[CH:5][C:6]([Br:9])=[N:7][CH:8]=1)(=[O:24])=[O:21]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 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), m-chloroperbenzoic acid (48 g, 0.19 mol) was added portionwise at 0° C. and the mixture was stirred for 2 hours at room temperature. Aqueous saturated 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 magnesium sulfate (MgSO4), and concentrated in vacuo gave the title compound (20.9 g, 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 magnesium sulfate (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ff7239a0753432da0ea0fc72e8237ae
Source dataset
uspto-grants-2003_01
Patent number
US06506779B1

Reaction notes

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