Trimethylsulfonium iodide → 2-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane

HRID 455327

Reaktionsgleichung

Reaktionsgleichung von HRID 455327
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1.[I-].C[S+](C)C>CS(C)=O.C(OCC)(=O)C>[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([C:12]2([C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=3)[CH2:1][O:13]2)=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 75127Trimethylsulfonium iodideHCID 15184934(4-Chlorophenyl)(4-iodophenyl)methanoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 593172172-(4-Chlorophenyl)-2-(4-iodophenyl)oxiraneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium tert-butoxide (18.48 g, 165.0 mmol) was added to a rapidly stirred suspension of 4-chloro-4′-iodobenzophenone (51.38 g, 150.0 mmol) and trimethylsulphonium iodide (33.66 g, 165.0 mmol) in dimethylsulphoxide (200 ml) and the resulting mixture was stirred at room temperature for 3 hours. The mixture was diluted with ethyl acetate (500 ml), washed with water (3×500 ml) and then with brine (500 ml). The organic layer was separated and the solvent removed in vacuo to afford (RS)-2-(4-chlorophenyl)-2-(4-iodophenyl)oxirane (53.48 g, 100%) as a pale yellow oil that solidified upon standing to afford an off-white solid. 1H NMR (DMSO-d6) 7.76 (2H, d), 7.45 (2H, d), 7.34 (2H, d), 7.12 (2H, d), 3.32 (2H, m). MS: [M−H]− 355.

Aufarbeitung

  1. washwashed with water (3×500 ml)
  2. customThe organic layer was separated
  3. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bc271e068b074e829a5fcbf4181e96a8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497294B2

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