Potassium Cyanide → 2-(3-Iodophenyl)acetonitrile

HRID 2372468Notes

Reaction equation

HRID 2372468 reaction equation
[C-:1]#[N:2].[K+].[I:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[I:4][C:5]1[CH:6]=[C:7]([CH2:8][C:1]#[N:2])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 27593613-Iodobenzyl bromide

Product 1

HCID 27593682-(3-Iodophenyl)acetonitrileYield 90.8%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of potassium cyanide (4 g) and tetra-n-butylammonium bromide (0.32 g) in water (20 ml) was added to a solution of 3-iodobenzyl bromide (5.92 g) in methylene chloride (20 ml) and the mixture was heated to reflux for 2 hours. The organic phase was separated, washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using methylene chloride as eluent to give 3-iodophenylacetonitrile (4.4 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-20be3f1d358c4cb0bd69adc6668daf23
Source dataset
uspto-grants-1992_03
Patent number
US05098930

Reaction notes

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