Dimethyl Sulfoxide → 4,4,5,5,6,6,7,7,7-Nonafluoroheptanecarbonitrile

HRID 1267464Notes

Reaction equation

HRID 1267464 reaction equation
I[CH2:2][CH2:3][C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8].[C-:17]#[N:18].[Na+].O.[CH3:21]S(C)=O>>[F:15][C:4]([F:16])([C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:2][CH2:21][C:17]#[N:18]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8929Sodium CyanideHCID 748871,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane

Product 1

HCID 185462924,4,5,5,6,6,7,7,7-NonafluoroheptanecarbonitrileYield 66%

Procedure

1-Iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane (10.0 g, 26.2 mmol) and sodium cyanide (3.85 g, 78.6 mmol) were stirred in dimethyl sulfoxide (50 ml) for 30 minutes at 60° C. Water was added to the reaction mixture, which was then extracted with ether. The resulting organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off to give 4,4,5,5,6,6,7,7,7-nonafluoroheptanecarbonitrile (4.7 g, Yield 66%) as a brown oil.

Workup

  1. extractionwas then extracted with ether
  2. washThe resulting organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-dbbcc3eabe514985a4ffe2600341a1c4
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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