Sodium Cyanide → 2-Bromobenzyl cyanide

HRID 1414209Notes

Reaction equation

HRID 1414209 reaction equation
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br>O.C(O)C>[Br:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][C:1]#[N:2]

Participants

5

Procedure

To a suspension of 220.0 g of sodium cyanide in 265 ml of water and 380 ml of absolute ethanol, is added, while stirring, a solution of 911.0 g of o-bromobenzyl bromide in 911 ml of ethanol. The reaction proceeds exothermally, but is eventually heated under reflux for about 0.5 hour, then cooled in an ice-bath, and filtered. The solid is washed with ether, the filtrate is concentrated, the residue is suspended in 300 ml of water and extracted with three 500 ml portions of ether. The ether extracts are washed, dried, and the solvent is removed. The residue is distilled to give 730 g of the named product, bp 141°-142° (12mm).

Workup

  1. additionis added
  2. temperatureis eventually heated
  3. temperatureunder reflux for about 0.5 hour
  4. temperaturecooled in an ice-bath
  5. filtrationfiltered
  6. washThe solid is washed with ether
  7. concentrationthe filtrate is concentrated
  8. extractionextracted with three 500 ml portions of ether
  9. washThe ether extracts are washed
  10. customdried
  11. customthe solvent is removed
  12. distillationThe residue is distilled

Sources & evidence

ORD record
ord-8063beaa59d7427ea7a95d092363c3bb
Source dataset
uspto-grants-1977_01
Patent number
US04001233

Reaction notes

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