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

HRID 1627

Reaction equation

HRID 1627 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f537d62089cd4cba9bc833054c2f705b
Source dataset
uspto-grants-1998_03
Patent number
US05726195

Linked notes

Loading…