Reaction #985271

Reaction equation

AIBN

4iodo-6,6,7,7,8,8,9,9,9-nonafluorononan-1-ol

phosphorous acid

triethylamine

→

6,6,7,7,8,8,9,9,9-Nonafluorononan-1-ol

Solvents

dioxane

dioxane

Conditions

Workup

1. 1
   Temperatureduring reflux
2. 2
   workup.ADDITIONAfter addition
3. 3
   Temperaturethe reaction mixture was refluxed for a period of time until the GLC analysis
4. 4
   Othera complete reaction (usually an hour)
5. 5
   ExtractionThe crude product was extracted into diethyl ether (3×50 cm3)
6. 6
   Dryingdried (MgSO4)
7. 7
   OtherThe solvent was removed in vacuo
8. 8
   Otherthe pure product was obtained by reduced pressure distillation as a colourless liquid

Procedure

A solution of AIBN (4.9 g, 30 mmol) in dioxane (150 cm3) was added dropwise into a solution of 4iodo-6,6,7,7,8,8,9,9,9-nonafluorononan-1-ol (Preparation 1B, 25 g, 58 mmol), phosphorous acid (19.1 g, 0.29 mol) and triethylamine (32.3 g, 0.32 mol) in dioxane (150 cm3) under an atmosphere of nitrogen during reflux. After addition, the reaction mixture was refluxed for a period of time until the GLC analysis revealed a complete reaction (usually an hour). The crude product was extracted into diethyl ether (3×50 cm3) and dried (MgSO4). The solvent was removed in vacuo and the pure product was obtained by reduced pressure distillation as a colourless liquid.

Source