Potassium Cyanide → 2-(2-Bromo-3-methylphenyl)acetonitrile
Reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9]Br.[C-:11]#[N:12].[K+]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:11]#[N:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
2-bromo-1-(bromomethyl)-3-methylbenzene (15 g, 0.057 mmol) and potassium cyanide (9.6 g, 0. 148 mol) were added to dimethylformamide (75 ml) and stirred at 90° C. overnight. The solvent was evaporated under reduced pressure and the residue partitioned between water (150 ml) and methylene chloride. The aqueous layer was extracted twice with methylene chloride, the organic extracts was separated, washed twice with water and was evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:methylene chloride (3:7) as eluent gave 8.0 g (67%) of the title compound.
Workup
- customThe solvent was evaporated under reduced pressure
- customthe residue partitioned between water (150 ml) and methylene chloride
- extractionThe aqueous layer was extracted twice with methylene chloride
- customthe organic extracts was separated
- washwashed twice with water
- customwas evaporated under reduced pressure
- customPurification of the residue by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-918cb1bb863a44b4bf4df26917291d17
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313137B1
Reaction notes
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