Sodium Cyanide → 2-(2-Bromo-4-chlorophenyl)acetonitrile

HRID 1021350Notes

Reaction equation

HRID 1021350 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9]Br.[C-:11]#[N:12].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:11]#[N:12]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 106130662-Bromo-1-(bromomethyl)-4-chlorobenzene

Product 1

HCID 218285012-(2-Bromo-4-chlorophenyl)acetonitrileYield 60.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-bromo-1-(bromomethyl)-4-chlorobenzene (9.8 g; 34.5 mmol) and sodium cyanide (2.0 g; 41.4 mmol) in 15 mL of 95% ethanol and 2.5 mL water was stirred and heated to reflux. After 30 minutes, the solvent was evaporated and the residue was partitioned between 100 mL ether and 50 mL water. The organic layer was dried over sodium sulfate and evaporated. The residual solid was washed out of the flask with hexane and collected by filtration, washed with hexane, and air-dried on the filter to give 4.82 g of 2-(2-bromo-4-chlorophenyl)acetonitrile as a light yellow solid.

Workup

  1. temperatureheated to reflux
  2. customthe solvent was evaporated
  3. customthe residue was partitioned between 100 mL ether and 50 mL water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. washThe residual solid was washed out of the flask with hexane
  7. filtrationcollected by filtration
  8. washwashed with hexane
  9. customair-dried on the
  10. filtrationfilter

Sources & evidence

ORD record
ord-32fdc4ae9d184e8cbc86b2a5508b876f
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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