Acetonitrile → 2-(Perfluorohexyl)ethylphosphonic acid
Reaction equation
C([O:3][P:4]([CH2:9][CH2:10][C:11]([F:29])([F:28])[C:12]([F:27])([F:26])[C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])(=[O:8])[O:5]CC)C.Br[Si](C)(C)C.CC#N>C(Cl)Cl.CO>[F:29][C:11]([F:28])([C:12]([F:26])([F:27])[C:13]([F:24])([F:25])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:18])([F:17])[F:19])[CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]Participants
Procedure
(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctyl)phosphonic acid diethyl ester (0.79 g, 1.6 mmol) was dissolved in CH2Cl2 (5 ml) under N2. Bromotrimethylsilane (0.8 ml, 6.1 mmol) was added via syringe and the mixture was stirred for 6 hours. Volatiles were removed in vacuo to give a thick orange oil; this was dissolved in MeOH (20 ml) with fuming to give a yellow solution. The mixture was stirred overnight and evaporated to dryness to give a pale yellow powder. Addition of MeCN caused separation of a white solid from the yellow solution. The solid was collected by filtration, affording the desired product as a white powder. Yield 0.56 g, 1.3 mmol, 82%. Analysis found (calculated) %: C, 22.35 (22.45); H, 1.25 (1.41). 1H NMR (d6-DMSO, 400 MHz, 298 K): δ 2.35 (m, 2H), 1.73 (m, 2H). 13C{1H} NMR (d6-DMSO, 100 MHz, 298 K): δ 121-105 (m, C-F coupling unresolved), 25.13 (t, JC-F=23 Hz), 17.10 (d, JC-P=138 Hz). 31P{1H} NMR (d6-DMSO, 162 MHz, 298 K): δ 22.87. MS (FAB, m/z): 429 ([M+H]+, 100%).
Workup
- customVolatiles were removed in vacuo
- customto give a thick orange oil
- customto give a yellow solution
- stirringThe mixture was stirred overnight
- customevaporated to dryness
- customto give a pale yellow powder
- customseparation of a white solid from the yellow solution
- filtrationThe solid was collected by filtration
Sources & evidence
- ORD record
- ord-e1a2641bb7be494fbecdaa3414dbcb52
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08405069B2
Reaction notes
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