Sodium Cyanide → 4-Iodophenylacetonitrile

HRID 1900097Notes

Reaction equation

HRID 1900097 reaction equation
[C-:1]#[N:2].[Na+].[I:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1>CS(C)=O.O>[I:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:1]#[N:2])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 9542584-Iodobenzyl bromide

Product 1

HCID 1428664-IodophenylacetonitrileYield 69.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4.36 g (20.0 mmol) of p-iodotoluene (purchased from Tokyo Kasei), 3.9 g (22 mmol) of N-bromosuccinimide (purchased from Tokyo Kasei) and 60 ml of carbon tetrachloride (purchased from Wako Junyaku Kogyo) was refluxed under the irradiation by means of an incandescent lamp for 4 hours to give 2.67 g (yield: 45.0%) of 4-iodobenzyl bromide (as a white crystalline). Subsequently, to 0.49 g (10 mmol) of sodium cyanide (purchased from Kokusan Kagaku) in 10 ml of dimethyl sulfoxide (purchased from Aldrich) solution heated at 50° C. was added 1.48 g (5.00 mmol) of the above 4-iodobenzyl bromide, the mixture was stirred at ambient temperature for 3 hours, the resultant reaction mass was dissolved in water and extracted with hexane, and hexane was removed to give 0.84 g (yield: 68.9%) of 4-iodophenylacetonitrile as a white crystalline.

Workup

  1. customthe resultant reaction mass
  2. extractionextracted with hexane, and hexane
  3. customwas removed

Sources & evidence

ORD record
ord-fa214a12bb224c0aa10536eaeffaa5cf
Source dataset
uspto-grants-1996_11
Patent number
US05574062

Reaction notes

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