Water → 1,1,1,2,2-Pentafluoro-8-iodooctane

HRID 1267744Notes

Reaction equation

HRID 1267744 reaction equation
[I-:1].[Na+].CS(O[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])(=O)=O.O>CC(C)=O>[I:1][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 185440091-Methanesulfonyloxy-7,7,8,8,8-pentafluorooctane

Product 1

HCID 120170661,1,1,2,2-Pentafluoro-8-iodooctaneYield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (19.62 g, 130 mmol) was added to a solution of 1-methanesulfonyloxy-7,7,8,8,8-pentafluorooctane (14 g, 47.01 mmol) in acetone (200 ml), followed by heating under reflux for 12 hours. After the reaction was completed, 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. The solvent was distilled off to give 1-iodo-7,7,8,8,8-pentafluorooctane (14 g, Yield 89%).

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. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ed04a7e51fe94b3fbd9d431443bbd434
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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