Dimethyl Sulfoxide → m-Trifluoromethylphenylacetonitrile

HRID 1494420Notes

Reaction equation

HRID 1494420 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.[C-:13]#[N:14].[Na+].CS(C)=O>O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH2:6][C:13]#[N:14])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 697163-(Trifluoromethyl)benzyl chloride

Product 1

HCID 75360m-TrifluoromethylphenylacetonitrileYield 107.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.0 g (61.5 mmole) m-trifluoromethylbenzyl chloride, 9.56 g (195 mmole) sodium cyanide and 60 ml dimethylsulfoxide was heated at 50° to 80° C. for four hours and poured into water. The aqueous mixture was extracted with methylene chloride, the extracts dried over sodium sulfate and the solvent evaporated in vacuo to give 12.2 g of yellow oil which was used in the next step.

Workup

  1. temperaturewas heated at 50° to 80° C. for four hours
  2. extractionThe aqueous mixture was extracted with methylene chloride
  3. dry with materialthe extracts dried over sodium sulfate
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-90fe399d604c4de58d6af10789a929dd
Source dataset
uspto-grants-1991_06
Patent number
US05026715

Reaction notes

Loading…