Water → 2,6-Difluorobenzylphosphonic acid

HRID 2041838Notes

Reaction equation

HRID 2041838 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][P:5](=[O:12])([O:9]CC)[O:6]CC.Br[Si](C)(C)C.O>ClCCl.CO>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][P:5](=[O:6])([OH:9])[OH:12]

Participants

6

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 86653411Diethyl 2,6-difluorobenzylphosphonate

Product 1

HCID 667303292,6-Difluorobenzylphosphonic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl 2,6-difluorobenzylphosphonate (2.00 g, 7.57 mmol) was dissolved in dry dichloromethane (20 mL). Bromotrimethylsilane (3.3 mL, 25 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 a white crystalline solid (1.199 g, 76% yield). 1H NMR (400.14 MHz, DMSO) δ 7.29 (m), 7.04 (m, 2H), 2.96 (d, J=20.99 Hz, 2H). 31P{1H} NMR (161.97 MHz, DMSO): δ 19.51. Analysis calculated (found) %: C, 40.40 (40.64), H, 3.39 (3.34).

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-36cfd0e3a80d48ac8655cf4960aabdba
Source dataset
uspto-grants-2013_11
Patent number
US08586208B2

Reaction notes

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