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

HRID 633557Notes

Reaction equation

HRID 633557 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 60C (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 and partitioned into ethyl acetate and cold water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous 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 (anhydrous Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf4598693ca34dc095286c6837bfb2c1
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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