Dimethylformamide → 3-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-pyridine

HRID 33529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33529
S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]([F:28])([F:27])[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]([CH2:25]O)[CH:22]=[N:23][CH:24]=2)=[CH:15][CH:14]=1>ClCCl>[Cl:3][CH2:25][C:21]1[CH:22]=[N:23][CH:24]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][C:11]([F:28])([F:27])[F:10])=[CH:14][CH:15]=2)[CH:20]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24729847(5-(4-(Trifluoromethoxy)phenyl)pyridin-3-yl)methanol

Produkt 1

HCID 691065193-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

136 mg (0.083 ml, 1.14 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.1 ml N,N-dimethylformamide (DMF) and 153 mg (0.57 mmol) [5-(4-Trifluoromethoxy-phenyl)-pyridin-3-yl]-methanol in 10 ml dichloromethane and stirred for 2 h at 0° C. The mixture was 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), evaporated and the obtained material (156 mg, 89%) used without further purification.

Aufarbeitung

  1. additionThe mixture was poured on ice/sodium bicarbonate solution
  2. customthe organic phase separated
  3. extractionThe water phase is extracted with dichloromethane
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (sodium sulphate)
  6. customevaporated
  7. customthe obtained material (156 mg, 89%) used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-71c7f54f53f94a33a4c52385eeadf0b6
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429605B2

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