Hydrochloric Acid → Triethylammonium 1,1,2,2-tetrafluoro-4-hydroxy-butane-1-sulfinate

HRID 571156Notes

Reaction equation

HRID 571156 reaction equation
Br[C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6].[S:11](S([O-])=O)([O-:13])=[O:12].[Na+].[Na+].[CH2:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:20].Cl>O.C(#N)C>[F:9][C:2]([F:10])([S:11]([O-:13])=[O:12])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6].[CH2:19]([NH+:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24489Sodium DithioniteHCID 27363694-Bromo-3,3,4,4-tetrafluorobutan-1-ol

Product 1

HCID 86660801Triethylammonium 1,1,2,2-tetrafluoro-4-hydroxy-butane-1-sulfinateYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A 1 L reactor was charged with 100.0 g (0.44 mole/1.0 equivalent) of 4-bromo-3,3,4,4-tetrafluorobutan-1-ol, 300 g of acetonitrile, 250 g of water, 108.2 g (0.62 mole/1.4 equivalent) of sodium dithionite and 53.4 g (0.52 mole/1.2 equivalents) of triethylamine, followed by 4 hours of stirring at 60° C. Upon confirming the termination of the reaction, the reaction liquid underwent cooling and 100 mL of 1N HCl was added thereto, followed by stirring. Subsequently, an organic layer was separated, and then the organic layer was subjected to distillation of the solvent, thereby obtaining 264 g of a target triethylammonium 1,1,2,2-tetrafluoro-4-hydroxy-butane-1-sulfinate. It exhibited a purity of 46% and a yield of 88% at this time.

Workup

  1. customthe termination of the reaction
  2. customthe reaction liquid underwent
  3. temperaturecooling
  4. stirringby stirring
  5. customSubsequently, an organic layer was separated
  6. distillationthe organic layer was subjected to distillation of the solvent

Sources & evidence

ORD record
ord-96823f07e58c450b88a404b7464c34ba
Source dataset
uspto-grants-2015_05
Patent number
US09024058B2

Reaction notes

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