2,5-Dibromopyridine → 5-Bromo-2-(methylthio)pyridine

HRID 971113Notes

Reaction equation

HRID 971113 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][S-:10].[Na+]>CN(C)C=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([S:10][CH3:9])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 693532,5-DibromopyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 114242515-Bromo-2-(methylthio)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,5-dibromopyridine and sodium thiomethoxide (1.3 eq) in N,N-dimethylformamide (2 ml/mmol) was stirred at room temperature for 20 minutes then cooled to 0° C. After diluting with cold water the precipitate was filtered to afford the 5-Bromo-2-methylthiopyridine compound as a solid.

Workup

  1. temperaturethen cooled to 0° C
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-805be5141cb245fd9a79796a7abfd520
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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