Potassium Cyanide → 2-(2-broMo-6-chlorophenyl)acetonitrile

HRID 1679892Notes

Reaction equation

HRID 1679892 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]Br)=[C:6]([Br:10])[CH:5]=[CH:4][CH:3]=1.[C-:11]#[N:12].[K+]>C(O)C.O>[Br:10][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:11]#[N:12]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 27568722-Bromo-6-chlorobenzyl bromide

Product 1

HCID 218500512-(2-broMo-6-chlorophenyl)acetonitrileYield 52.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 31.3 g of the crude 6-chloro-alpha,2-dibromotoluene in 100 ml of warm ethanol is treated with a solution of 6.7 g of potassium cyanide in 10 ml of water and the mixture is heated at reflux for 4 hours. The crude product is isolated by pouring the cooled reaction mixture into water and filtering the resulting precipitate. Recrystallization of this solid from aqueous ethanol then gives 12.4 g of 2-bromo-6-chlorophenylacetonitrile, mp 82°-84° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 4 hours
  3. customThe crude product is isolated
  4. additionby pouring
  5. filtrationfiltering the resulting precipitate
  6. customRecrystallization of this solid from aqueous ethanol

Sources & evidence

ORD record
ord-45979b60a7864976b5230c3fe1fdad1e
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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