Potassium Cyanide → m-Trimethylsilylbenzylcyanide

HRID 1265947Notes

Reaction equation

HRID 1265947 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][Si:5]([CH3:15])([CH3:14])[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9]Br>C(N(CCCC)CCCC)CCC.O>[CH3:4][Si:5]([CH3:15])([CH3:14])[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][C:1]#[N:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 12583977(3-(Bromomethyl)phenyl)trimethylsilane

Product 1

HCID 18547281m-TrimethylsilylbenzylcyanideYield 55%

Reagents, catalysts & solvents 2

HCID 7622TributylamineCatalystHCID 962WaterSolvent

Procedure

A mixture of KCN (5.5 g, 84 mmol), m-trimethylsilylbenzylbromide (5.31 g, 21.8 mmol), tributylamine (0.11 g, 0.59 mmol) and water (12.5 cm3) was stirred overnight. The product was extracted with dichloromethane (3×30 cm3), the extract was filtered through a silica plug (5g) and the solvent was removed under reduced pressure. The residue was distilled to give the product (2.27 g, 55%) as a colorless liquid.

Workup

  1. extractionThe product was extracted with dichloromethane (3×30 cm3)
  2. filtrationthe extract was filtered through a silica plug (5g)
  3. customthe solvent was removed under reduced pressure
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-d700a913003940b09f7670b3d8e8ad2c
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

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