Hydrogen Bromide → 10-Bromo-1,1,1,2,2,3,3,4,4-nonafluorodecane

Temperature

100 °C

To a mixture of 18.00 g of 6-(nonafluorobutyl)-1-hexanol and 225 mL of 48 weight percent hydrobromic acid was slowly added 23 mL of concentrated sulfuric acid. The reaction mixture was heated at 100° C. for 12 hr and poured into 1 liter of water. The mixture was extracted with hexanes, and the combined organic phases were then washed with saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. The hexanes solution was concentrated to a light amber liquid, which was eluted through 2 inches (5 cm) of silica with hexanes. Concentration of the eluent yielded a light amber liquid, and bulb-to-bulb distillation gave 18.29 g of 1-bromo-6-(nonafluorobutyl)hexane as a clear, colorless liquid, b.p. 70-80° C. at 0.05 torr (7 Pa).

1. extractionThe mixture was extracted with hexanes
2. washthe combined organic phases were then washed with saturated aqueous sodium bicarbonate
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationThe hexanes solution was concentrated to a light amber liquid, which
5. washwas eluted through 2 inches (5 cm) of silica with hexanes
6. customConcentration of the eluent yielded
7. distillationa light amber liquid, and bulb-to-bulb distillation

ORD record

ord-38ce5a3ded8e446197f4b8471f0f548d

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06824882B2