2-Bromo-5-nitropyridine → 2-(Methylthio)-5-nitropyridine

HRID 1789657Notes

Reaction equation

HRID 1789657 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][S-:12].[Na+]>CN(C=O)C>[CH3:11][S:12][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 782402-Bromo-5-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 44393132-(Methylthio)-5-nitropyridineYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.0 g (9.85 mmol) 2-bromo-5-nitropyridine dissolved in 8 mL DMF was added 690 mg (9.85 mmol) of sodium thiomethoxide. The mixture was stirred at room temperature for 1 h, and partitioned between ethyl acetate and water, dried over MgSO4 and concentrated to obtain 1.13 g of 2-methylthio-5-nitro-pyridine, pure by 1H NMR.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-077245168e9a4c2d9bc2b8f2bc81de07
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

Loading…