Diethyl (4-fluorophenyl)phosphonate → (4-Fluorophenyl)phosphonic acid

HRID 84989Notes

Reaction equation

HRID 84989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:15])([O:12]CC)[O:9]CC)=[CH:4][CH:3]=1>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([P:8](=[O:9])([OH:15])[OH:12])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 13508438Diethyl (4-fluorophenyl)phosphonate

Product 1

HCID 12670622(4-Fluorophenyl)phosphonic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Diethyl 4-fluorophenylphosphonate (600 mg, 2.55 mmol) was combined with 8M HCl (10 mL, excess) and the mixture refluxed overnight. The reaction was cooled and filtered to remove dark specks. The solvent was removed under vacuum until a solid began to form. The mixture was then put in the refrigerator for several hours. The solid was dried to yield an off-white powder (P80 mg). 1H NMR (400.14 MHz, DMSO) δ 7.71 (ddd, J=12.49, 8.52, 5.99 Hz, 2H), 7.28 (ddd, J=9.02, 9.02, 2.65 Hz, 2H). 31P{1H} NMR (161.97 MHz, DMSO): δ 12.81. Analysis calculated (found) %: C 40.93 (40.33), H 3.43 (3.49).

Workup

  1. temperaturethe mixture refluxed overnight
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customto remove dark specks
  5. customThe solvent was removed under vacuum until a solid
  6. customto form
  7. waitThe mixture was then put in the refrigerator for several hours
  8. customThe solid was dried
  9. customto yield an off-white powder (P80 mg)

Sources & evidence

ORD record
ord-b4a9abcc4cb343e59433aa372beaa56a
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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