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

HRID 2041840Notes

Reaction equation

HRID 2041840 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-277c865f332b46abaee6991c20812382
Source dataset
uspto-grants-2013_11
Patent number
US08586208B2

Reaction notes

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