Acetonitrile → 2-(5-Bromo-2-chlorophenyl)acetonitrile

HRID 1625881Notes

Reaction equation

HRID 1625881 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]=1

Participants

4

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

  1. additionAdded
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed successively with water, 10% aqueous hydrochloric acid solution
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, and dried over sodium sulfate
  6. 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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