Hydrochloric Acid → 2-Chloro-5-nitrophenyl 3-chloro-2-thienyl ketone

HRID 48965

Reaktionsgleichung

Reaktionsgleichung von HRID 48965
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:10]=[CH:9][S:8][CH:7]=1.[Cl:11][C:12]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:13]=1[C:14](Cl)=[O:15].Cl>C(Cl)Cl>[Cl:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:14]([C:13]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:12]=1[Cl:11])=[O:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 870173-ChlorothiopheneHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 206342582-Chloro-5-nitrophenyl 3-chloro-2-thienyl ketoneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of aluminum chloride (1.33 g, 0.0102 mol) and methylene chloride is added 3-chlorothiophene (1.21 g, 0.0102 mol) dropwise. The resultant mixture is stirred 30 minutes and treated with a solution of 2-chloro-5-nitrobenzoyl chloride (2.20 g, 0.0100 mol) in methylene chloride. The resultant mixture is stirred overnight at room temperature, poured into ice, acidified with concentrated hydrochloric acid and extracted twice with methylene chloride. The combined organic layers are washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to a brown oil. Trituration with ether affords the title compound as a brown solid (1.33 g, 44.0%, mp 114-116° C.) which is identified by NMR spectral analysis.

Aufarbeitung

  1. additionpoured into ice
  2. extractionextracted twice with methylene chloride
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo to a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-b88bd5e8fc374d8eaafcec445099e04a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706663B2

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