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

HRID 548534Notes

Reaction equation

HRID 548534 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-73912055f8974039a5f53bec2e067fe8
Source dataset
uspto-grants-2011_05
Patent number
US07943567B2

Reaction notes

Loading…