Acetic Acid → 1,1,1,2-Tetrafluoro-8-thiocyanato-2-trifluoromethyl-octane

HRID 1879615Notes

Reaction equation

HRID 1879615 reaction equation
[S-:1][C:2]#[N:3].[K+].C(O)(=O)C.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([F:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18]>C(O)C>[F:18][C:17]([F:19])([F:20])[C:16]([F:25])([C:21]([F:22])([F:23])[F:24])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][S:1][C:2]#[N:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516872Potassium thiocyanateHCID 58901159HCID 58901159, compound

Product 1

HCID 589012511,1,1,2-Tetrafluoro-8-thiocyanato-2-trifluoromethyl-octaneYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In accordance with scheme (45) above, 8-Bromo-1,1,1,2-tetrafluoro-2-trifluoromethyl-octane (20 grams) can be dissolved in 30 mL of ethanol containing 7.6 grams of potassium thiocyanate. Acetic acid (0.2 mL) can be added to form a mixture and the mixture heated to reflux for 4 hours. The mixture can be allowed to cool to room temperature overnight, concentrated under vacuum, and partitioned between methylene chloride (200 mL) and water (100 mL). The organic layer can be dried over magnesium sulfate, filtered, and concentrated under vacuum to afford 18.2 grams (97%) 1,1,1,2-tetrafluoro-8-thiocyanato-2-trifluoromethyl-octane by NMR analysis.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated under vacuum
  4. custompartitioned between methylene chloride (200 mL) and water (100 mL)
  5. dry with materialThe organic layer can be dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2ef1f4a3a80b44a6979e463d908dd5d3
Source dataset
uspto-grants-2012_11
Patent number
US08318656B2

Reaction notes

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