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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1401428Erstellt: 25. Oktober 2026

Dimethyl Sulfoxide → 2-(3-Chloro-4-fluorophenyl)-2-methyloxirane

https://huagongshe.com/reaction/1401428

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDimethyl SulfoxideHCID 679—
EduktSodium hydrideHCID 24758—
EduktTrimethylsulfonium iodideHCID 75127—
Edukt3'-Chloro-4'-fluoroacetophenoneHCID 520422—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt2-(3-Chloro-4-fluorophenyl)-2-methyloxiraneHCID 59455250—

Reaktionsbedingungen

Temperatur65 °C

Reaktionsschritte

DMSO is added to NaH (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents were stirred for 10 min. after which the solution of 1-(3-chloro-4-fluorophenyl)ethanone (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h; the reaction is monitored by LCMS. After completion, the reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get the crude product.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08907097B2
Quelldatensatzuspto-grants-2014_12
ORD IDord-a9b1ab4428bb4af79245994fffdac574
Quellennotizuspto-grants-2014_12