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

HRID 1006697

Reaction equation

HRID 1006697 reaction equation
[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C-:11]#[N:12].[K+]>CN(C)C=O>[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:11]#[N:12]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 109343202-Bromo-1-(bromomethyl)-3-methylbenzene

Product 1

HCID 226726132-(2-Bromo-3-methylphenyl)acetonitrileYield 44.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-brom-3-methylbenzylbromide (25 g, 0.095 mol) and potassium cyanide (16 g, 0.25 mol) in dimethylformamide (100 ml) was stirred at 90° C. for 20 h. The solvent was evaporated under reduced pressure and to the residue were added toluene and water. The organic layer was separated washed with water, separated and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride as eluent gave 8.8 g (44%) of the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure and to the residue
  2. additionwere added toluene and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. customseparated
  6. customevaporated under reduced pressure
  7. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-9ba3ef7949d34f6181be2d166926885e
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Linked notes

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