Water → HCID 58262208, compound

HRID 84981Notes

Reaction equation

HRID 84981 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:18])[C:16]=1[F:17])[CH2:5][P:6](=[O:13])([O:10]CC)[O:7]CC.Br[Si](C)(C)C.O>ClCCl.CO.C(#N)C>[F:18][C:15]1[CH:14]=[C:4]([CH:3]=[C:2]([F:1])[C:16]=1[F:17])[CH2:5][P:6](=[O:7])([OH:10])[OH:13]

Participants

7

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 86653409HCID 86653409, compound

Product 1

HCID 58262208HCID 58262208, compoundYield 89.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl 3,4,5-trifluorobenzylphosphonate (2.80 g, 9.92 mmol) was dissolved in dry dichloromethane (30 mL). Bromotrimethylsilane (4.1 mL, 31.7 mmol) was added via syringe. The reaction was capped with a greased glass stopper and allowed to stir for 6 hours. The volatiles were removed under reduced pressure to yield a yellow oil. This was dissolved in 10:1 methanol:water (20 mL) and allowed to stir overnight. After removing the solvents, recrystallization in acetonitrile yielded large white needles (2.00 g, 89% yield). 1H NMR (400.14 MHz, DMSO) δ 7.16 (m, 2H), 2.99 (d, J=21.4 Hz, 2H). 13C {1H} NMR (100.62 MHz, DMSO) δ 149.9 (dddd, J=246, 9.6, 3.6, 3.6 Hz, 2C), 137.5 (dtd, J=247, 15.4, 3.7), 132.1-131.8 (m), 114.4-114.1 (m, 2C), 34.42 (d, J=132 Hz). 31P {1H} NMR (161.97 MHz, DMSO): δ 20.54. Analysis calculated (found) %: C 37.19 (37.17), H 2.67 (2.63). MS (FAB, m/z): 227 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 227.00849 (227.00670).

Workup

  1. customThe reaction was capped with a greased glass stopper
  2. customThe volatiles were removed under reduced pressure
  3. customto yield a yellow oil
  4. stirringto stir overnight
  5. customAfter removing

Sources & evidence

ORD record
ord-68f0f3c63624447686cdbb56c3f331c3
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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