Sodium methanethiolate → 3-Bromo-2-(2,4-difluorophenoxy)-5-(methylthiomethyl)pyridine

HRID 930936Notes

Reaction equation

HRID 930936 reaction equation
[Br:1][C:2]1[C:3]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.[CH3:19][S-:20].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:3]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[N:4][CH:5]=[C:6]([CH2:8][S:20][CH3:19])[CH:7]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 867210763-Bromo-5-(bromomethyl)-2-(2,4-difluorophenoxy)pyridine

Product 1

HCID 867210773-Bromo-2-(2,4-difluorophenoxy)-5-(methylthiomethyl)pyridineYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 311c (0.75 g, 1.979 mmol) and sodium thiomethoxide (0.139 g, 1.979 mmol) were combined in dimethylformamide (3.96 mL), stirred for 4 hours at ambient temperature, and partitioned into ethyl acetate and cold water. The organic layer was washed with saturated aqueous sodium chloride, dried (Na2SO4), filtered, and concentrated to afford the title compound (0.66 g, 96%).

Workup

  1. custompartitioned into ethyl acetate and cold water
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-392c5e1d80c748c29dac0e5e9e1e4d5c
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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