Ethanol → Ethyl 2-iodotetrafluoropropionate

HRID 963584

Reaction equation

HRID 963584 reaction equation
[F-].[K+].[CH2:3]([OH:5])[CH3:4].S(F)([O:9][C:10](F)(F)[C:11]([F:17])([I:16])[C:12]([F:15])([F:14])[F:13])(=O)=O>O>[I:16][C:11]([F:17])([C:12]([F:15])([F:14])[F:13])[C:10]([O:5][CH2:3][CH3:4])=[O:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 522689Potassium FluorideHCID 125963661,1,2,3,3,3-Hexafluoro-2-iodopropyl sulfurofluoridate

Product 1

HCID 12119967Ethyl 2-iodotetrafluoropropionateYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A 500 mL flask was charged with potassium fluoride (17.5 g, 0.31 mol) and absolute ethanol (110 mL), and was cooled in an ice-water bath. 2-iodo-hexafluoropropyl fluorosulfate (112.8 g, 0.3 mol) was added slowly. The reaction was exothermic and the reaction temperature was controlled at 20°-25° C. After addition was complete, the reaction mixture was heated at 70° C. for 4 hr and then poured into cold water. The bottom organic layer was separated, washed with saturated NaCl aqueous solution and dried over MgSO4. Evaporation of the solvent in vacuo followed by distillation gave 50 g (56% yield) of ethyl 2-iodotetrafluoropropionate product, formula above, having a boiling point of 60°-65° C. at 50 mmHg.

Workup

  1. temperaturewas cooled in an ice-water bath
  2. customwas controlled at 20°-25° C
  3. additionAfter addition
  4. customThe bottom organic layer was separated
  5. washwashed with saturated NaCl aqueous solution
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent in vacuo
  8. distillationfollowed by distillation

Sources & evidence

ORD record
ord-4cb0ea9eda0648f09d96a439cc915e21
Source dataset
uspto-grants-1998_06
Patent number
US05763552

Linked notes

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