Hydrogen Bromide → 15-Bromo-1,1,1,2,2,3,3,4,4-nonafluoropentadecane

Temperature

100 °C

To a mixture of 19.52 g of CF3(CF2)3(CH2)10CH2OH and 200 mL of 48 weight percent aqueous 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 CF3(CF2)3(CH2)10CH2Br as a clear, colorless liquid, b.p. 120-170° C. at 0.06 torr (8 Pa).

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

ORD record

ord-eb884160ef1c40799c3f8637dae67a18

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06841079B2