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

HRID 1739649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739649
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 21836291Pyridine, 5-bromo-2-(methylthio)-3-(trifluoromethyl)-Ausbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6882abcf675c45eb89ae7cf68e04e503
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05968875

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