Sodium methanethiolate → Pyridine, 5-bromo-2-(methylthio)-3-(trifluoromethyl)-

HRID 1739649Notes

Reaction equation

HRID 1739649 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[CH3:13][S-:14].[Na+]>CS(C)=O>[CH3:13][S:14][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 218363025-Bromo-2-chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 21836291Pyridine, 5-bromo-2-(methylthio)-3-(trifluoromethyl)-Yield 67.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The product of Example 6 (3.0 g, 0.012 mol) was dissolved with stirring in dimethyl sulphoxide (30 mL) and sodium methanethiolate (1.2 g, 0.017 mol) was added. The mixture was stirred at room temperature overnight, poured into ice-water, and extracted with hexane (2×50 mL). The organic extracts were combined, washed with water and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and purification of the residue by chromatography over silica (10% ethyl acetate:hexane) gave 2-methylthio-3-trifluoromethyl-5-bromopyridine (2.2 g) as a clear oil.

Workup

  1. extractionextracted with hexane (2×50 mL)
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customEvaporation of the solvent
  5. customunder reduced pressure and purification of the residue by chromatography over silica (10% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-6882abcf675c45eb89ae7cf68e04e503
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

Loading…