Bromotrimethylsilane → P-(12,12,13,13,14,14,15,15,15-Nonafluoropentadecyl)phosphonic acid
Reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([F:32])([F:31])[C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>ClCCl>[P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([F:31])([F:32])[C:21]([F:29])([F:30])[C:22]([F:27])([F:28])[C:23]([F:24])([F:25])[F:26])([OH:6])([OH:5])=[O:3]Participants
4
Procedure
To a solution of 15.23 g of 1-(diethylphosphono)-11-(nonafluorobutyl)undecane in 40 mL of dichloromethane was added 11.50 g of bromotrimethylsilane. After 24 hr at room temperature, the solution was concentrated to a pale yellowish liquid, and the intermediate silylphosphonate ester was dissolved in 200 mL of methanol. The resultant solution was stirred at room temperature for 30 min and concentrated to a white solid. Dissolution in methanol and concentration were repeated two times, and two recrystallizations of the crude product from heptane gave 10.85 g of 1-phosphono-11-(nonafluorobutyl)undecane (CF3(CF2)3(CH2)11PO3H2) as colorless plates, m.p. 93-96° C.
Workup
- concentrationthe solution was concentrated to a pale yellowish liquid
- dissolutionthe intermediate silylphosphonate ester was dissolved in 200 mL of methanol
- concentrationconcentrated to a white solid
- dissolutionDissolution in methanol
- concentrationconcentration
- customtwo times, and two recrystallizations of the crude product from heptane
Sources & evidence
- ORD record
- ord-4508aaf4303e4cfea632ef6560fb3ff9
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06824882B2
Reaction notes
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