Diethyl (4-fluorophenyl)phosphonate → (4-Fluorophenyl)phosphonic acid
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]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe mixture refluxed overnight