Water → 4-Iodophenylacetonitrile

HRID 1082257Notes

Reaction equation

HRID 1082257 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.O>CS(C)=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 3

HCID 962WaterHCID 8929Sodium CyanideHCID 9542584-Iodobenzyl bromide

Product 1

HCID 1428664-IodophenylacetonitrileYield 69.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a hot solution (50° C.) of sodium cyanide 0.49 g, 10.0 mmom, purchased from Kokusan Kagaku) in 10 ml of dimethyl sulfoxide (purchased from Aldrich) was added the above 4-iodobenzyl bromide (1.48 g, 5.0 mmol) and the mixture was stirred for three hours at ambient temperature. To the resultant reaction mass was added water and extracted with hexane. The solvent was removed to give 0.84 g (yield: 69%) of 4-iodophenylacetonitrile as a white crystalline.

Workup

  1. customTo the resultant reaction mass
  2. extractionextracted with hexane
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-b859884a88ee44e48976729a446fed30
Source dataset
uspto-grants-1996_12
Patent number
US05589506

Reaction notes

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