3,5-Dibromopyridine → 3-Bromo-5-(methylthio)pyridine

HRID 24030Notes

Reaction equation

HRID 24030 reaction equation
[CH3:1][S-:2].[Na+].[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1>CN(C=O)C.C(OCC)(=O)C>[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([S:2][CH3:1])[CH:10]=1

Participants

5

Reactant 2

HCID 693693,5-DibromopyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 223903593-Bromo-5-(methylthio)pyridineYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium thiomethoxide (1.6 g, 23 mmol) was added to a solution of 3,5-dibromopyridine (5 g, 21 mmol) in DMF (25 mL). After stirring overnight at room temperature, the reaction mixture was diluted with ethyl acetate and washed several times with brine. The extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude material was chromatographed on silica (10% ethyl acetate/hexanes) to give the title compound (3.8 g, 89% yield) as a clear oil.

Workup

  1. washwashed several times with brine
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe crude material was chromatographed on silica (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-11737b78fb724acd8db7cec523a3fce8
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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