Dimethyl Sulfoxide → 2-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane

HRID 45545

Reaktionsgleichung

Reaktionsgleichung von HRID 45545
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=2)=[O:20])=[CH:15][CH:14]=1>C(OCC)(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=3)[CH2:8][O:20]2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 15184934(4-Chlorophenyl)(4-iodophenyl)methanone

Produkt 1

HCID 593172172-(4-Chlorophenyl)-2-(4-iodophenyl)oxiraneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in oil, 128 mg, 3.2 mmol) was placed under N2 then DMSO (5 mL) was added. Trimethylsulfonium iodide (0.66 g, 3.2 mmol) was added as a solid after 15 min, followed after a further 30 min by (4-chloro-phenyl)-(4-iodo-phenyl)-methanone. The mixture was stirred at room temperature for 24 hours then diluted with ethyl acetate and washed with 1:2 water/brine, water and brine (×2). The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (1.01 g, 97%), which was used without further purification. LCMS (PS-A2) Rt 4.07 min [M−H]+ 355.

Aufarbeitung

  1. washwashed with 1:2 water/brine, water and brine (×2)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9fb6f5778b0846c0a20c64ea1f2da994
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541461B2

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