Sodium Chloride → 4-[(5-Nitro-thien-2-yl)ethynyl]benzonitrile

HRID 1627

Reaktionsgleichung

Reaktionsgleichung von HRID 1627
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)#[CH:2].Br[C:12]1[S:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1.C(N(CC)CC)C.[Cl-].[Na+]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[N+:17]([C:14]1[S:13][C:12]([C:2]#[C:1][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[CH:16][CH:15]=1)([O-:19])=[O:18]

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 832222-Bromo-5-nitrothiopheneHCID 45472454-Ethynylbenzonitrile

Produkt 1

HCID 196919534-[(5-Nitro-thien-2-yl)ethynyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-ethynylbenzonitrile (0.5 g), 2-bromo-5-nitrothiophene (0.9 g) and bis(triphenylphosphine)palladium dichloride (83 mg) in anhydrous dimethylformamide (4 ml) was added triethylamine (2.2 ml). The reaction mixture was stirred at room temperature for 3 days then ethyl acetate (200 ml) and saturated sodium chloride (200 ml) were added. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude solid was triturated with 1:1 dichloromethane/hexane followed by diethyl ether to give 4-[(5-nitro-2-thienyl)ethynyl]benzonitrile as a yellow solid.

Aufarbeitung

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe crude solid was triturated with 1:1 dichloromethane/hexane

Quellen und Nachweise

ORD-Eintrag
ord-f537d62089cd4cba9bc833054c2f705b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726195

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