Benzyl Bromide → Phenylacetonitrile

HRID 1578998Notes

Reaction equation

HRID 1578998 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C-]#N.[CH3:11][N:12]([S+](N(C)C)N(C)C)C>C(#N)C>[CH2:2]([C:11]#[N:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7498Benzyl Bromide2×HCID 19784595HCID 19784595, compound

Product 1

HCID 8794PhenylacetonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 1.71-g (10 mmole) sample of α-bromotoluene was injected into a solution of 1.90 g (10 mmole) of tris(dimethylamino)sulfonium cyanide in 2.4 ml (1.9 g) acetonitrile, and the mixture was shaken. The mixture became warm. After cooling, analysis by gas chromatography showed that all of the α-bromotoluene had been consumed, benzyl cyanide was formed in 95% yield, and benzyl isocyanide was formed in 5% yield. Crystals of tris(dimethylamino)sulfonium bromide separated from the reaction mixture.

Workup

  1. temperatureThe mixture became warm
  2. temperatureAfter cooling
  3. customhad been consumed

Sources & evidence

ORD record
ord-4dd762d79294494b84a2bf4371bc9e22
Source dataset
uspto-grants-1976_02
Patent number
US03940402

Reaction notes

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