Dimethyl Sulfoxide → 5,5,6,6,6-Pentafluorohexanecarbonitrile

HRID 1267735Notes

Reaction equation

HRID 1267735 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])(=O)=O.[C-:16]#[N:17].[Na+].O.[CH3:20]S(C)=O>C1OCCOCCOCCOCCOCCOC1>[F:14][C:9]([F:15])([C:10]([F:13])([F:12])[F:11])[CH2:8][CH2:7][CH2:6][CH2:20][C:16]#[N:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8929Sodium CyanideHCID 120170564,4,5,5,5-Pentafluoropentyl methanesulfonate

Product 1

HCID 185462625,5,6,6,6-PentafluorohexanecarbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Conditions

Temperature
100 °C

Procedure

1-Methanesulfonyloxy-4,4,5,5,5-pentafluoropentane (138 g, 538.62 mmol) was dissolved in dimethyl sulfoxide (1000 ml). Sodium cyanide (55.57 g, 1.077 mol) and 18-crown-6 (2.85 g, 10.77 mmol) were added to the solution followed by stirring for 2 hours at 100° C. After cooling to room temperature, water was added to the reaction mixture, which was then extracted twice with ether. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off to give 5,5,6,6,6-pentafluorohexanecarbonitrile (108 g, Yield 100%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionwas then extracted twice with ether
  3. washThe combined organic layers were washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-7677d0dbc822422eb28192a53fa766da
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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