Sodium Cyanide → 2-(3-Bromo-5-methoxyphenyl)acetonitrile

HRID 542738Notes

Reaction equation

HRID 542738 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH2:7]Br.[C-:12]#[N:13].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH2:7][C:12]#[N:13])[CH:9]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 122764491-Bromo-3-(bromomethyl)-5-methoxybenzene

Product 1

HCID 212429652-(3-Bromo-5-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the crude benzyl bromide and sodium cyanide (4.9 g, 0.1 m) in ethanol (500 ml) is stirred at 65° for 16 hours. The mixture is cooled, filtered and concentrated in vacuo. The residue is partitioned between water and chloroform and the chloroform phase is washed, dried with sodium sulfate and concentrated in vacuo to afford 5-bromo-3-methoxyphenylacetonitrile.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between water and chloroform
  5. washthe chloroform phase is washed
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea350897b76f41108096fdac08595c38
Source dataset
uspto-grants-1987_04
Patent number
US04659706

Reaction notes

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