Dimethyl Sulfoxide → 1,1,1-Trifluoro-2-(4-fluorophenyl)-prop-2-ene oxide

HRID 1401434

Reaktionsgleichung

Reaktionsgleichung von HRID 1401434
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[F:12][C:13]([F:24])([F:23])[C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:15]>C1COCC1>[F:24][C:13]([F:12])([F:23])[C:14]1([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH2:8][O:15]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 75127Trimethylsulfonium iodide

Produkt 1

HCID 145169411,1,1-Trifluoro-2-(4-fluorophenyl)-prop-2-ene oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

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 stirred for 10 min. after which the solution of 2,2,2-trifluoro-1-(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. 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.

Aufarbeitung

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture is cooled to 0° C
  3. additionis added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

Quellen und Nachweise

ORD-Eintrag
ord-182f1717fc644ecb8ac65237d5449714
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907097B2

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