Dimethylformamide → (Benzo[b]thiophen-5-yl)acetonitrile

HRID 546251Notes

Reaction equation

HRID 546251 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1.[C-]#N.[Na+].[CH3:15][N:16](C)C=O>O>[S:7]1[CH:8]=[CH:9][C:5]2[CH:4]=[C:3]([CH2:2][C:15]#[N:16])[CH:11]=[CH:10][C:6]1=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 111604985-(Bromomethyl)benzo[b]thiophene

Product 1

HCID 20509997(Benzo[b]thiophen-5-yl)acetonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round bottom flask was placed 5-bromomethyl-benzo[b]thiophene (5.27 g, 23.20 mmol), sodium cyanide (1.59 g, 32.49 mmol) and N,N-dimethylformamide (50 mL) and it was stirred for 24 h at 25° C. After this time, the reaction mixture was dissolved in water (30 mL) and extracted with ethyl acetate (3×30 mL), dried over sodium sulfate and purified on an AnaLogix Intelliflash system (120 g column, 3% ethyl acetate/hexanes to 20% ethyl acetate/hexanes) to afford benzo[b]thiophen-5-yl-acetonitrile (2.23 g, 55%) as a yellow solid.

Workup

  1. customIn a round bottom flask was placed
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialdried over sodium sulfate
  4. custompurified on an AnaLogix Intelliflash system (120 g column, 3% ethyl acetate/hexanes to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-45efb2b55a474136b9f9c03e90329fae
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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