Reaction #2504157

Reaction equation

11-(nonafluorobutyl)-1-undecanol

hydrobromic acid

sulfuric acid

→

1-bromo-1-(nonafluorobutyl)undecane

Solvents

water

Conditions

Workup

1. 1
   ExtractionThe mixture was extracted with hexanes
2. 2
   Washthe combined organic phases were washed with saturated aqueous sodium bicarbonate
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   ConcentrationThe solution was concentrated to an amber liquid, which
5. 5
   Washwas eluted through 3 inches of silica with hexanes
6. 6
   OtherConcentration of the eluent yielded
7. 7
   workup.DISTILLATIONa light amber liquid, and bulb-to-bulb distillation

Procedure

To a mixture of 19.52 g of 11-(nonafluorobutyl)-1-undecanol and 200 mL of 48 weight percent hydrobromic acid was slowly added 20 mL of concentrated sulfuric acid. The reaction mixture was heated at 100° C. for 24 hr and poured into 1 liter of water. The mixture was extracted with hexanes, and the combined organic phases were washed with saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. The solution was concentrated to an amber liquid, which was eluted through 3 inches of silica with hexanes. Concentration of the eluent yielded a light amber liquid, and bulb-to-bulb distillation gave 19.82 g of 1-bromo-1-(nonafluorobutyl)undecane as a clear, colorless liquid, b.p. 120-170° C. at 0.06 torr (8 Pa).

Source