Diethyl Ether → 1-Phenyl-2-methylbenzothiophenium triflate

HRID 432538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432538
[CH3:1][C:2]1[S:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[O-:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[C:19]1([I+]C2C=CC=CC=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C>O.C([O-])(=O)C1C=CC=CC=1.[Cu+2].C([O-])(=O)C1C=CC=CC=1>[O-:14][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:13])=[O:11].[C:19]1([S+:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[CH:3]=[C:2]2[CH3:1])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 709522-Methylbenzo(b)thiopheneHCID 2737137Diphenyliodonium trifluoromethanesulfonate

Produkt 1

HCID 111324971-Phenyl-2-methylbenzothiophenium triflateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 164650Cupric benzoateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Methylthianaphthene (5 g, 0.0327 mole), diphenyliodonium triflate (18.28 g, 0.0425 mole) and copper benzoate (0.1 g, 0.000327 mole) were heated without solvent for 0.5 hours at 140° C. under a nitrogen atmosphere. After cooling down, 150 ethyl ether was added to solidify the product. Filtration and washing with ethyl ether yielded a brownish-grey solid, which was dissolved in 500 ml hot water, and the solution filtered and the water removed in vacuo. The resulting off-white solid was stirred in 50 ml ethyl ether for 1 hour, the mixture filtered and the residue washed with ethyl ether. The product was recrystallized from dichloromethane/t-butyl methyl ether to yield 8.97 g (76%) of 1-phenyl-2-methylbenzothiophenium triflate. The structure was confirmed by 1H/13C NMR spectroscopy.

Aufarbeitung

  1. temperatureAfter cooling down
  2. filtrationFiltration
  3. washwashing with ethyl ether
  4. customyielded a brownish-grey solid, which
  5. filtrationthe solution filtered
  6. customthe water removed in vacuo
  7. filtrationthe mixture filtered
  8. washthe residue washed with ethyl ether
  9. customThe product was recrystallized from dichloromethane/t-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1d3098c42c4f473e98fc013543f933f0
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664022B1

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