تفاعل #1723

ord-f537d62089cd4cba9bc833054c2f705b

معادلة التفاعل

[Cl-].[Na+]
sodium chloride
C#Cc1ccc(C#N)cc1
4-ethynylbenzonitrile
O=[N+]([O-])c1ccc(Br)s1
2-bromo-5-nitrothiophene
CCN(CC)CC
triethylamine
N#Cc1ccc(C#Cc2ccc([N+](=O)[O-])s2)cc1
4-[(5-nitro-2-thienyl)ethynyl]benzonitrile

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تجفيفThe organic layer was dried over anhydrous sodium sulfate
  2. 2
    ترشيحfiltered
  3. 3
    أخرىevaporated to dryness
  4. 4
    أخرىThe crude solid was triturated with 1:1 dichloromethane/hexane

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05726195uspto-grants-1998_03