Thionyl Chloride → 3-(Chloromethyl)-5-[4-(trifluoromethyl)phenyl]isoxazole

HRID 585074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585074
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14]O)[CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:20])=O>ClCCl>[Cl:20][CH2:14][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)[O:13][N:12]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 22064161{5-[4-(Trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-ol

Produkt 1

HCID 220642603-(Chloromethyl)-5-[4-(trifluoromethyl)phenyl]isoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

{5-[4-(Trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-ol (200 mg) was dissolved in dry dichloromethane (10 ml), and cooled to 0° C. The solution was stirred while adding a solution of thionyl chloride (2.74 ml) in dichloromethane (25 ml), then allowed to warm to room temperature and stirred overnight. Solvent was evaporated under reduced pressure, and the residue was purified by preparative thin layer chromatography, eluting with 30% ethyl acetate/hexane, to afford 3-(chloromethyl)-5-[4-(trifluoromethyl)phenyl]isoxazole, a compound of formula (25).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customSolvent was evaporated under reduced pressure
  4. customthe residue was purified by preparative thin layer chromatography
  5. washeluting with 30% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c13309e4d15e4250802c821fc9ed2cb1
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06930111B2

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