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

HRID 385921Notes

Reaction equation

HRID 385921 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH3:9][S-:10].[Na+]>CN(C=O)C.C(OCC)C>[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 4378561Sodium methanethiolate

Product 1

HCID 125608072-Bromo-6-(methylthio)pyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dibromopyridine (0.50 g, 2.11 mmol) in DMF (21 mL) was added sodium thiomethoxide (0.16 g, 2.32 mmol) and the solution was allowed to react overnight. The solution was then diluted with ethyl ether, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography to yield the title compound. 1H NMR (600 MHz, CDCl3): 7.32 (t, J=7.3 Hz, 1H), 7.15 (dd, J=9.6, 1.2 Hz, 1H), 7.12 (dd, J=9.0, 0.6 Hz, 1H), 2.55 (s, 1H).

Workup

  1. customto react overnight
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-037800bddd094d2f92df5be1f7a9acda
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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