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Cumene → (Chloromethyl)(isopropylphenyl)(phenyl)sulfonium triflate

HRID 926958
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 926958
[C:1]1([S:7]([CH2:9][Cl:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([CH:17]([CH3:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F:20][C:21]([F:34])([F:33])[S:22]([O:25]S(C(F)(F)F)(=O)=O)(=[O:24])=[O:23]>C(OCC)C>[O-:25][S:22]([C:21]([F:34])([F:33])[F:20])(=[O:24])=[O:23].[Cl:10][CH2:9][S+:7]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:17]([CH3:19])[CH3:18])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7406CumeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81624Chloromethyl phenyl sulfoxide

Produkt 1

HCID 86699374(Chloromethyl)(isopropylphenyl)(phenyl)sulfonium triflate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Chloromethyl phenyl sulfoxide (170 mg, 1.1 mmol) of example 21 was dissolved in dry diethyl ether (5 mL) under an argon atmosphere. Cumene (145 mg, 1.1 eq) was added to the previous solution and the mixture was cooled to a temperature below −60° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.184 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred until the reaction was complete. The orange precipitated triflate salt was quickly filtered at −60° C. affording 0.399 g as orange viscous oil after heating at room temperature, which was a mixture by proton NMR.

Aufarbeitung

  1. temperaturethe mixture was cooled to a temperature below −60° C
  2. additionwas added slowly
  3. temperaturemaintaining the same temperature
  4. customThe orange precipitated triflate salt
  5. filtrationwas quickly filtered at −60° C.
  6. customaffording 0.399 g as orange viscous oil

Quellen und Nachweise

ORD-Eintrag
ord-7225fceb28cc423fa14a0d43ccb84cd2
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09290446B2

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