Water → 3,5-Difluorobenzylphosphonic acid

HRID 84985Notes

Reaction equation

HRID 84985 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[CH2:5][P:6](=[O:13])([O:10]CC)[O:7]CC.Br[Si](C)(C)C.O>ClCCl.CO>[F:17][C:15]1[CH:14]=[C:4]([CH:3]=[C:2]([F:1])[CH:16]=1)[CH2:5][P:6](=[O:7])([OH:13])[OH:10]

Participants

6

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 11219261(3,5-Difluoro-benzyl)-phosphonic acid diethyl ester

Product 1

HCID 667303683,5-Difluorobenzylphosphonic acidYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl 3,5-difluorobenzylphosphonate (3.00 g, 11.4 mmol) was dissolved in dry dichloromethane (25 mL). Bromotrimethylsilane (4.9 mL, 37 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 8:1 methanol:water (25 mL) and allowed to stir overnight. After removing the solvents, recrystallization in acetonitrile yielded a white crystalline solid (1.98 g, 91% yield). 1H NMR (400.14 MHz, DMSO) δ 7.05 (dt, J=9.49, 2.09 Hz), 6.95 (d, J=8.54 Hz, 2H), 3.02 (d, J=21.57 Hz, 2H). 31P {1H} NMR (161.97 MHz, DMSO): δ 20.63. Analysis calculated (found) %: C 40.40(40.67), H 3.39 (3.39).

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
  6. customthe solvents, recrystallization in acetonitrile

Sources & evidence

ORD record
ord-dabf6a65a8d24ac1a2ecf3ac8565d798
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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