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

HRID 1047978Notes

Reaction equation

HRID 1047978 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-f4ed9b45f27841a2ba4410f88a412cfe
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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