Potassium Cyanide → 2-(1-Benzothiophen-2-yl)acetonitrile

HRID 635368Notes

Reaction equation

HRID 635368 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1.[C-:12]#[N:13].[K+].O1CCOCC1>O>[S:7]1[C:3]([CH2:2][C:12]#[N:13])=[CH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]1=2

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 312751,4-DioxaneHCID 128138372-(Chloromethyl)-1-benzothiophene

Product 1

HCID 126319232-(1-Benzothiophen-2-yl)acetonitrileYield 44.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-chloromethylbenzo[b]thiophene (21 g), potassium cyanide (11.7 g), 1,4-dioxane (200 ml) and water (100 ml) was stirred and heated under reflux for 4 hours, then cooled to ambient temperature and diluted with water (200 ml). The product was extracted into toluene (3×200 ml), then the combined extracts were washed with water (2×300 ml), dried (Na2SO4), and the solvents were removed in vacuo. The residue was purified via flash chromatography over silica using a 1:4 mixture of ethyl acetate and petroleum ether (b.p. 60-80° C.) as eluant. Appropriate fractions were combined and the solvents were removed in vacuo to give benzo[b]thiophen-2-acetonitrile as a yellow solid (8.9 g), m.p. 59-61° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. extractionThe product was extracted into toluene (3×200 ml)
  4. washthe combined extracts were washed with water (2×300 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvents were removed in vacuo
  7. customThe residue was purified via flash chromatography over silica using
  8. additiona 1:4 mixture of ethyl acetate and petroleum ether (b.p. 60-80° C.) as eluant
  9. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-cecc8a2f33a442469214c09540500b03
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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