2,6-Dibromopyridine → 2-Bromo-6-(methylthio)pyridine

HRID 860984Notes

Reaction equation

HRID 860984 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH3:9][S:10]C.[Na]>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:10][CH3:9])[N:3]=1

Participants

5

Reactant 2

HCID 122742,6-DibromopyridineHCID 86593196Sodium methylsulfide

Product 1

HCID 125608072-Bromo-6-(methylthio)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2,6-dibromopyridine. (1.0 eq.) in DMSO (0.3M) was added sodium methylsulfide (1.1 eq.). The mixture was stirred for 2 d at rt then poured in water. The resulting precipitate was filtered off and the filtrate was extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound as a colorless oil.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. extractionthe filtrate was extracted with Et2O (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9f6bac72d53c438aab03cc88ef2edaf3
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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