Reaktion #624440

Reaktionsgleichung

4-Chloro-2-(trifluoromethyl)pyridine

1,8-diazabicyclo[5.4.0]undec-7-ene

phenylmethanethiol

→

4-(benzylthio)-2-(trifluoromethyl)pyridine

Ausbeute 75.5%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between ether (25 mL) and water (25 mL)
2. 2
   ExtraktionThe aqueous layer was extracted with ether (2×25 mL)
3. 3
   Trocknenthe combined organic layers were dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigeto give a pale yellow oil
7. 7
   SonstigeThe crude product was purified by chromatography on silica gel (gradient: 0-30% ethyl acetate in isohexane)

Vorschrift

4-Chloro-2-(trifluoromethyl)pyridine (141 μl, 1.102 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (199 μl, 1.322 mmol), and phenylmethanethiol (129 μl, 1.102 mmol) were dissolved in dry dimethylformamide (2 mL). The reaction mixture was heated at 100° C. in a microwave for 30 minutes, then partitioned between ether (25 mL) and water (25 mL). The aqueous layer was extracted with ether (2×25 mL) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give a pale yellow oil. The crude product was purified by chromatography on silica gel (gradient: 0-30% ethyl acetate in isohexane) to afford 4-(benzylthio)-2-(trifluoromethyl)pyridine (224 mg) as a colourless oil. LCMS (Method F, ES-API): RT 2.79 min, m+H=270.1.

Quelle