Potassium Cyanide → 2-(3-Bromo-5-methylphenyl)acetonitrile

HRID 1643355Notes

Reaction equation

HRID 1643355 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9]Br)[CH:3]=1.[C-:11]#[N:12].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH2:9][C:11]#[N:12]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene

Product 1

HCID 236288332-(3-Bromo-5-methylphenyl)acetonitrileYield 39.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-bromo-3-(bromomethyl)-5-methylbenzene (6.56 kg, 0.1515 M) in ethanol (20 L) were added potassium cyanide (2.38 kg, 36.55 mol) and distilled water (10 L) in this order. The mixture was refluxed for 3 hours. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate (30 L) and brine (20 L). The organic layer was dried with magnesium sulfate (2 kg) and concentrated under reduced pressure to give a brown-colored oil. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:9) to afford 3-bromo-5-methylbenzyl cyanide (2.06 kg, 9.81 mol, 39%) as a pale brown oil.

Workup

  1. distillationdistilled water (10 L) in this order
  2. temperatureThe mixture was refluxed for 3 hours
  3. customthe mixture was evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate (30 L) and brine (20 L)
  5. dry with materialThe organic layer was dried with magnesium sulfate (2 kg)
  6. concentrationconcentrated under reduced pressure
  7. customto give a brown-colored oil
  8. customThe crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:9)

Sources & evidence

ORD record
ord-fad7634dfb3e44c68b2ba4b7c6169076
Source dataset
uspto-grants-2012_02
Patent number
US08119800B2

Reaction notes

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