Potassium Cyanide → (3-Chloro-2-methoxyphenyl)acetonitrile

HRID 1444448Notes

Reaction equation

HRID 1444448 reaction equation
C1C(=O)[N:5](Br)[C:3](=O)C1.[Cl:9][C:10]1[C:11]([O:17][CH3:18])=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=1.[C-]#N.[K+]>C(Cl)(Cl)(Cl)Cl.O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:9][C:10]1[C:11]([O:17][CH3:18])=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][C:3]#[N:5]

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 67184N-bromobutanimideHCID 134345771-Chloro-2-methoxy-3-methylbenzene

Product 1

HCID 17989277(3-Chloro-2-methoxyphenyl)acetonitrileYield 81.1%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

39.4 g (221.3 mmol) of NBS and 100 mg of benzoyl peroxide are added to 31.6 g (201.7 mmol) of 3-chloro-2-methoxytoluene in 500 ml of CCl4. It is refluxed over 16 hours, allowed to cool and filtered. Solvent is removed from the filtrate, and the filtrate is dissolved in 214 ml of N,N-dimethylformamide and 142 ml of water. 20.9 g (322.1 mmol) of potassium cyanide is added at 0C and stirred over 16 hours. The reaction mixture is diluted with water and extracted several times with methyl tert-butyl ether. The organic phase is washed several times with saturated sodium chloride solution and dried on sodium sulfate. The solvent is removed in a vacuum and after chromatographic purification on silica gel (hexane/ethyl acetate 20%), 29.7 g of product is obtained.

Workup

  1. temperatureIt is refluxed over 16 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. customSolvent is removed from the filtrate
  5. dissolutionthe filtrate is dissolved in 214 ml of N,N-dimethylformamide
  6. extractionextracted several times with methyl tert-butyl ether
  7. washThe organic phase is washed several times with saturated sodium chloride solution
  8. customdried on sodium sulfate
  9. customThe solvent is removed in a vacuum
  10. customafter chromatographic purification on silica gel (hexane/ethyl acetate 20%)

Sources & evidence

ORD record
ord-1ae660e71960419e847343ab8afe24cd
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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