2,2,3,3-Tetrafluoro-1-propanol → 2,2,3,3-Tetrafluoropropyl nonafluorobutane-1-sulfonate

HRID 1091989Notes

Reaction equation

HRID 1091989 reaction equation
[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][OH:4].[H-].[Na+].[F:11][C:12]([F:27])([S:23](F)(=[O:25])=[O:24])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16]>CCOCC>[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][O:4][S:23]([C:12]([F:11])([F:27])[C:13]([F:21])([F:22])[C:14]([F:19])([F:20])[C:15]([F:18])([F:17])[F:16])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 24758Sodium hydrideHCID 67814Perfluoro-1-butanesulfonyl fluoride

Product 1

HCID 235052222,2,3,3-Tetrafluoropropyl nonafluorobutane-1-sulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2,2,3,3-Tetrafluoropropanol (2.64 g) was added to a suspension of sodium hydride (1.08 g) in dry ether (50 ml) at 0° C. under an argon atmosphere. Stirred at 0° C. for 15 minutes. Perfluoro-1-butanesulphonyl fluoride (12.08 g) was slowly added. Stirred at reflux for 3 hours, cooled and carefully quenched with H2O. Extracted with ether, twice. The combined extracts were washed with saturated brine, dried over MgSO4, filtered and evaporated to give 2,2,3,3-tetrafluoropropyl-1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulphonate as an oil. Yield 5.47 g. NMR Spectrum: (CDCl3) δ 5.9 (tt, 1H), 4.75 (t, 2H).

Workup

  1. stirringStirred
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. customcarefully quenched with H2O
  5. extractionExtracted with ether
  6. washThe combined extracts were washed with saturated brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-f5574c22c50a4fdd9a409ded6cf54b4f
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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