Dimethylformamide → 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine
Reaktionsgleichung
S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:13]=[C:14]([C:18]2[N:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1>ClCCl>[Cl:3][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:27])([F:26])[F:10])[CH:13]=2)=[N:23][CH:22]=1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
911 mg (0.56 ml, 7.66 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 970 mg (3.83 mmol) [6-(3-Trifluoromethyl-phenyl)-pyridine-3-yl]-methanol in 30 ml dichloromethane, stirred for 5 min. at 0° C., and at r.t. for 1 h. The mixture is poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), and evaporated. Purification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 750 mg (72%) of 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine as light yellow crystals
Aufarbeitung
- waitat r.t. for 1 h
- additionThe mixture is poured on ice/sodium bicarbonate solution
- customthe organic phase separated
- extractionThe water phase is extracted with dichloromethane
- washThe combined organic phases were washed with water
- dry with materialdried (sodium sulphate)
- customevaporated
- customPurification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3)
Quellen und Nachweise
- ORD-Eintrag
- ord-d6c9e3c17fa240de9127e0949efdfbda
- Quelldatensatz
- uspto-grants-2008_09
- Patentnummer
- US07429605B2
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