Trichloroacetyl chloride → 5-(p-Chlorophenyl)pyrrol-5-yl trichloromethyl ketone

HRID 375189

Reaktionsgleichung

Reaktionsgleichung von HRID 375189
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.C(OCC)(=O)C>[Cl:1][C:2]([C:3]([C:15]1([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=2)[N:16]=[CH:17][CH:18]=[CH:19]1)=[O:4])([Cl:7])[Cl:6]

Komponenten

6

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 11430Potassium CarbonateHCID 2724282-(4-Chlorophenyl)-1h-pyrrole

Produkt 1

HCID 189303945-(p-Chlorophenyl)pyrrol-5-yl trichloromethyl ketoneAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of trichloroacetyl chloride (11.26 g, 0.0619 mol) in ether is treated with a solution of 2-(p-chlorophenyl)pyrrole (10.0 g, 0.0503 mol) in ether, stirred for four hours at room temperature, treated with saturated potassium carbonate solution and diluted with ethyl acetate. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow solid. The solid is recrystallized from 2-propanol to give the title product as a yellow solid (12.63 g, mp 166°-168° C.) which is identified by 1HNMR spectral analysis.

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow solid
  6. customThe solid is recrystallized from 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-010d6e87a7bd461486de42f79cf78067
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484807

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