Reaktion #172187

Reaktionsgleichung

diethyl 11-(perfluorobenzyloxy)undecylphosphonate

bromotrimethylsilane

water

→

11-(perfluorobenzyloxy)undecylphosphonic acid

Ausbeute 92.0%

Lösungsmittel

dichloromethane

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe system was sealed with a greased stopper
2. 2
   SonstigeVolatiles were removed under reduced pressure
3. 3
   Sonstigeto produce a viscous, brown oil, which
4. 4
   workup.STIRRINGto stir for six hours
5. 5
   SonstigeAfter removal of solvent under reduced pressure an off white solid
6. 6
   Sonstigeformed
7. 7
   Sonstigewhich was recrystallized from a minimal amount of acetonitrile

Vorschrift

A solution of diethyl 11-(perfluorobenzyloxy)undecylphosphonate (0.63 g, 1.3 mmol) in 15 mL of dry dichloromethane and 0.7 mL (5.3 mmol) bromotrimethylsilane was made. The system was sealed with a greased stopper and allowed to stir overnight. Volatiles were removed under reduced pressure to produce a viscous, brown oil, which was dissolved in 25 mL of a 4:1 methanol:water solution and allowed to stir for six hours. After removal of solvent under reduced pressure an off white solid formed, which was recrystallized from a minimal amount of acetonitrile to afford white crystals of 11-(perfluorobenzyloxy)undecylphosphonic acid (0.49 g, 92%). 1H NMR (399.9 MHz, DMSO-d6) δ 4.55 (s, 2H), 3.42 (t, J=6.4 Hz, 2H), 1.49-1.44 (m, 6H), 1.34-1.18 (m, 14H). 13C{1H} NMR (100.5 MHz, DMSO-d6) δ 104.5, 69.9, 58.8, 30.1, 29.9, 28.9, 28.8, 28.8, 28.7, 28.1, 26.8, 25.4, 22.648 (d, J=4.8 Hz). 31P{1H} NMR (161.91 MHz, DMSO-d6): δ 27.63. 19F NMR (376.3 MHz, DMSO-d6): δ −141.86 (m, 2F), −152.95 (m, 1F), −160.88 (m, 2F), from trifluoro acetic acid. Analysis calculated (found): C 50.00 (50.16), H 6.06 (6.23), F 21.97 (21.79). Exact mass calculated (found) for [M−H]−, m/z: 432.1489 (432.1487).

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