Hydrogen Bromide → 19-Bromo-1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluorononadecane
Reaction equation
[F:1][C:2]([F:37])([C:33]([F:36])([F:35])[F:34])[C:3]([F:32])([F:31])[C:4]([F:30])([F:29])[C:5]([F:28])([F:27])[C:6]([F:26])([F:25])[C:7]([F:24])([F:23])[C:8]([F:22])([F:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]O.[BrH:38].S(=O)(=O)(O)O>O>[Br:38][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([F:21])([F:22])[C:7]([F:23])([F:24])[C:6]([F:25])([F:26])[C:5]([F:27])([F:28])[C:4]([F:29])([F:30])[C:3]([F:31])([F:32])[C:2]([F:1])([F:37])[C:33]([F:34])([F:35])[F:36]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
To a mixture of 29.0 g of crude 11-(heptadecafluorooctyl)-1-undecanol and 250 mL of 48% hydrobromic acid was slowly added 25 mL of concentrated sulfuric acid. The reaction mixture was heated at 100° C. for 18 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 a dark liquid, which was eluted through 3 inches of silica with hexanes. Concentration of the eluent afforded 20.2 g of crude 1-bromo-11-(heptadecafluorooctyl)undecane as a nearly white solid, which was used without further purification.
Workup
- extractionThe mixture was extracted with hexanes
- washthe combined organic phases were washed with saturated aqueous sodium bicarbonate
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe solution was concentrated to a dark liquid, which
- washwas eluted through 3 inches of silica with hexanes
Sources & evidence
- ORD record
- ord-9aa331cdd6d144129208ee13d902ab0b
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06824882B2
Reaction notes
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