Water → 6-Iodo-1,1,1,2,2-pentafluorohexane

HRID 1267738Notes

Reaction equation

HRID 1267738 reaction equation
[I-:1].[Na+].CS(O[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])(=O)=O.O>CC(C)=O>[I:1][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 120170601-Methanesulfonyloxy-5,5,6,6,6-pentafluorohexane

Product 1

HCID 120170616-Iodo-1,1,1,2,2-pentafluorohexaneYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (168 g, 1.12 mol) was added to a solution of 1-methanesulfonyloxy-5,5,6,6,6-pentafluorohexane (101 g, 373.77 mmol) in acetone (2000 ml), followed by heating under reflux for 12 hours. Water was added to the reaction mixture, which was then extracted twice with ether. The combined organic layers were washed with 1% aqueous sodium thiosulfate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: pentane) to give 1-iodo-5,5,6,6,6-pentafluorohexane (93.6 g, Yield 83%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 12 hours
  3. extractionwas then extracted twice with ether
  4. washThe combined organic layers were washed with 1% aqueous sodium thiosulfate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel column chromatography (eluent: pentane)

Sources & evidence

ORD record
ord-1d73ac716b1c4483af3d69d15f32935f
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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