Acetonitrile → 2-(5-Bromo-2-chlorophenyl)acetonitrile
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7]Cl.[C:11](#[N:13])C>[C-]#N.C([N+](CC)(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH2:7][C:11]#[N:13])[CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The above 5-bromo-2-chlorobenzyl chloride was dissolved in acetonitrile (100 ml), and the mixture was cooled to 0° C. Added thereto was tetraethylammonium cyanide (8.8 g), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed successively with water, 10% aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give 5-bromo-2-chlorophenylacetonitrile as a pale yellow solid, which was used in the subsequent step without further purification.
Workup
- additionAdded
- customThe solvent was evaporated under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate
- washThe solution was washed successively with water, 10% aqueous hydrochloric acid solution
- dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, and dried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-40ba5598b76b4196a4c57391dda16386
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785403B2
Reaction notes
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