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

HRID 496805Notes

Reaction equation

HRID 496805 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][S-:10].[Na+].O>CN(C)C=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([S:10][CH3:9])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 693532,5-DibromopyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 114242515-Bromo-2-(methylthio)pyridineYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-dibromo pyridine (5 g) was mixed with sodium thiomethoxide (1.4 g) and dissolved in dimethylformamide (30 ml) and then, refluxed for 5 hours. After completing the reaction, water was added to dilute and extracted with ethylacetate to separate an organic layer. The separated organic layer was dried with anhydrous magnesium sulfate, distilled under reduced pressure, and separated by performing a silica gel attributed chromatography (ethylacetate:normal hexane=1:15) As a result, 5-bromo-2-methylsulfanyl pyridine (3.47 g, yield: 80%) was obtained as an oil phase.

Workup

  1. temperaturerefluxed for 5 hours
  2. additionwas added
  3. additionto dilute
  4. extractionextracted with ethylacetate
  5. customto separate an organic layer
  6. dry with materialThe separated organic layer was dried with anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customseparated

Sources & evidence

ORD record
ord-296a57016b4743889237515d4eeacbc9
Source dataset
uspto-grants-2005_09
Patent number
US06946558B2

Reaction notes

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