Water → HCID 86664729, compound

HRID 85005Notes

Reaction equation

HRID 85005 reaction equation
[F:1][C:2]([F:34])([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][P:26](=[O:33])([O:30]CC)[O:27]CC)[C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([F:11])=[C:5]([F:12])[C:4]=1[F:13].Br[Si](C)(C)C.O>ClCCl.CO>[F:34][C:2]([F:1])([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][P:26](=[O:27])([OH:33])[OH:30])[C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([F:11])=[C:5]([F:12])[C:4]=1[F:13]

Participants

6

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 86664730HCID 86664730, compound

Product 1

HCID 86664729HCID 86664729, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  1. customThe system was sealed with a greased stopper
  2. customVolatiles were removed under reduced pressure
  3. customto produce a viscous, brown oil, which
  4. stirringto stir for six hours
  5. customAfter removal of solvent under reduced pressure an off white solid
  6. customformed
  7. customwhich was recrystallized from a minimal amount of acetonitrile

Sources & evidence

ORD record
ord-3b86692d97c1425ca878f3adc3fe3c3b
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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