Hydrogen Bromide → 19-Bromo-1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluorononadecane
Reaction equation
[C:1]([C:5]([C:8]([C:11]([C:14]([C:17]([C:20]([C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]O)([F:25])[F:24])([F:22])[F:21])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2].[BrH:38].S(=O)(=O)(O)O>O>[C:1]([C:5]([C:8]([C:11]([C:14]([C:17]([C:20]([C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][Br:38])([F:25])[F:24])([F:22])[F:21])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
To a mixture of 29.0 g (0.049) of CF3(CF2)7(CH2)10CH2OH and 250 mL of 48 percent by weight aqueous 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 (8 cm) of silica with hexanes. Concentration of the eluent yielded 20.2 g of CF3(CF2)7(CH2)10CH2Br 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 (8 cm) of silica with hexanes
Sources & evidence
- ORD record
- ord-4fee1fa98df34143861aaa7a0089a4ed
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06841079B2
Reaction notes
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