Water → 2-Bromobenzyl cyanide

HRID 1443177Notes

Reaction equation

HRID 1443177 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.O.[C-:11]#[N:12].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:11]#[N:12]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 769652-Bromobenzyl bromide

Product 1

HCID 296252-Bromobenzyl cyanideYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 g (100 mmol) of 2-bromobenzyl bromide is mixed in 100 ml of N,N-dimethylformamide and 64 ml of water with 9.75 g (150 mmol) of potassium cyanide and stirred overnight at room temperature. The reaction mixture is poured into ice water. After being extracted three times with methyl tert-butyl ether, the combined organic extracts are washed with brine, dried, and the solvent is spun off. The residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 18.9 g (96.4%) of the desired compound is obtained.

Workup

  1. extractionAfter being extracted three times with methyl tert-butyl ether
  2. washthe combined organic extracts are washed with brine
  3. customdried
  4. customThe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-131a3c19e0c54f08965e6eebbce5c5cd
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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