Trimethylsilyl triflate → Diphenyliodonium trifluoromethanesulfonate

HRID 2232044

Reaktionsgleichung

Reaktionsgleichung von HRID 2232044
[Cl-].[C:2]1([I+:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:15]([Si](C)(C)C)[S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17]>C(Cl)Cl>[O-:18][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:17])=[O:15].[C:9]1([I+:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 65367Trimethylsilyl triflateHCID 73870Diphenyliodonium chloride

Produkt 1

HCID 2737137Diphenyliodonium trifluoromethanesulfonateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

Into a 500 mL flask was placed 300 mL of distilled methylene chloride (distilled from P2O5) and 5.0 g (16 mmol) of commercial diphenyliodonium chloride (Aldrich Chemical Co.). The heterogeneous mixture was stirred vigorously in a water bath at 22° C. and 3.19 ml (3.91 g, 17.6 mmol) of trimethylsilyl triflate was added. The solid dissolved almost immediately but a precipitate reappeared after 5 m. The reaction was stirred for 15 h and the solvent removed on the rotary evaporator. The residue was triturated with ether to yield 6.5 g (96%) of the iodonium triflate 1 (mp 165°-8° C.). The material tested negative for chloride with silver nitrate-ethanol. The aryl iodonium triflates 3 and 4 were produced in a similar fashion.

Aufarbeitung

  1. customInto a 500 mL flask was placed
  2. dissolutionThe solid dissolved almost immediately
  3. stirringThe reaction was stirred for 15 h
  4. customthe solvent removed on the rotary evaporator
  5. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-25f14e11c0d3469f93660b95f5227abc
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04786441

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