Acetonitrile → Sodium 1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfinate

HRID 2421455Notes

Reaction equation

HRID 2421455 reaction equation
Br[C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6].C(#N)C.C(=O)([O-])O.[Na+:18].[S:19](S([O-])=O)([O-:21])=[O:20].[Na+].[Na+]>O>[F:9][C:2]([F:10])([S:19]([O-:21])=[O:20])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6].[Na+:18]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 27363694-Bromo-3,3,4,4-tetrafluorobutan-1-ol

Product 1

HCID 58037024Sodium 1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfinateYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2 litter reactor was charged with 151 g (0.67 mol) of 4-bromo-3,3,4,4-tetrafluorobutan-1-ol, 600 ml of acetonitrile, 600 ml of water, 112 g (1.33 mol/2.0 equivalent)) of sodium hydrogencarbonate, and 235 g (1.35 mol/2.0 equivalent) of sodium dithionite in a nitrogen stream. The mixture was stirred at room temperature for 12 hours. The reaction solution was extracted four times with 500 ml of acetonitrile. The solvent was evaporated from the resulting organic layer to obtain 120 g of the target sodium 1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfinate. The purity of the product was 80% and the yield was 77%.

Workup

  1. extractionThe reaction solution was extracted four times with 500 ml of acetonitrile
  2. customThe solvent was evaporated from the resulting organic layer

Sources & evidence

ORD record
ord-08d44b0454f045e3a8bd121f3569c8dd
Source dataset
uspto-grants-2011_06
Patent number
US07956142B2

Reaction notes

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