Sodium methanethiolate → HCID 68756332, compound

HRID 712779Notes

Reaction equation

HRID 712779 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.[CH3:10][S-:11].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][S:11][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 149329483-Bromo-5-(bromomethyl)pyridine

Product 1

HCID 68756332HCID 68756332, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-5-bromomethyl-pyridine (7.5 g, 30 mmol) is dissolved in EtOH (200 mL). The solution is cooled down to 0° C. Sodium thiomethoxide (3.1 g, 45 mmol) is added slowly and the reaction mixture is stirred for 16 hrs. Then the solvent is removed, water and EtOAc are added. The aqueous layer is separated and extracted with EtOAc. Organic layers are combined and concentrated to give 6.0 g of the 3-bromo-5-methylsulfanylmethyl-pyridine.

Workup

  1. customThen the solvent is removed
  2. additionwater and EtOAc are added
  3. customThe aqueous layer is separated
  4. extractionextracted with EtOAc
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75ccd43aaee64bffbd201e16328c53a8
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…