Diethyl Ether → 4'-Nitro-3'-[2-(trifluoromethyl)phenylthio]acetophenone

HRID 1087186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087186
Cl[C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[F:14][C:15]([F:24])([F:23])[C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[S-:18].[Li+].CCOCC.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[N+:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11](=[O:13])[CH3:12])=[CH:3][C:2]=1[S:18][C:17]1[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=1[C:15]([F:14])([F:23])[F:24])([O-:10])=[O:9]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 104427551-(3-Chloro-4-nitrophenyl)ethanoneHCID 67871513Lithium 2-(trifluoromethyl)thiophenoxide

Produkt 1

HCID 102466754'-Nitro-3'-[2-(trifluoromethyl)phenylthio]acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 3'-chloro-4'-nitroacetophenone (2.7 g) in toluene (50 ml) was added to a stirred solution of lithium 2-(trifluoromethyl)thiophenoxide [4.4 g; Aust. J. Chem. 32 2313 (1979)]in ether (142 ml) at 0° C. The mixture was stirred at room temperature for 2 hours and refluxed for 20 minutes. The resulting mixtures were added ethyl acetate and water, and the organic layer was washed with water, dried and evaporated. The oily residue was purified by column chromatography on silica gel (70 g) eluting with toluene to give a yellow oil of 4'-nitro-3'-[2-(trifluoromethyl)phenylthio]acetophenone (1.3 g).

Aufarbeitung

  1. customat 0° C
  2. temperaturerefluxed for 20 minutes
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customThe oily residue was purified by column chromatography on silica gel (70 g)
  7. washeluting with toluene

Quellen und Nachweise

ORD-Eintrag
ord-dc4702a2dac9434bb54d0b0ac3a1712f
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034417

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