Sodium Cyanide → 2-(2-Fluorophenyl)propanenitrile

HRID 637613Notes

Reaction equation

HRID 637613 reaction equation
[C-:1]#[N:2].[Na+].[F:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[CH:7](Cl)[CH3:8]>CS(C)=O>[F:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[CH:7]([C:1]#[N:2])[CH3:8]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 135643251-(1-Chloroethyl)-2-fluorobenzene

Product 1

HCID 133880122-(2-Fluorophenyl)propanenitrileYield 85.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

In 300 ml of dimethyl sulfoxide was dissolved 35 g of sodium cyanide by heating at 90° C., and 45 g of 2-fluoro-α-methylbenzyl chloride was added. The mixture was stirred at 90° C. for 4 hours, and then cooled. Ice-water was added and the mixture was extracted with n-hexane. The n-hexane layer was washed with water and dried over anhydrous magnesium sulfate and the solvent was evaporated off. The residue obtained was purified by distillation under reduced pressure to afford 36 g of 2-fluoro-α-methylbenzyl cyanide, b.p.0.5 55° C.

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with n-hexane
  3. washThe n-hexane layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated off
  6. customThe residue obtained
  7. distillationwas purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-b4950e3dd7e146fd8c32b508fa2be13f
Source dataset
uspto-grants-1985_12
Patent number
US04557871

Reaction notes

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