2,2-Di{4-[difluoro(phosphono)methyl]benzyl}malonic acid, dibenzyl ester → 2,2-Di{4-[Difluoro(Phosphono)Methyl]Benzyl}Malonic Acid

HRID 566499Notes

Reaction equation

HRID 566499 reaction equation
[F:1][C:2]([F:49])([P:45]([OH:48])([OH:47])=[O:46])[C:3]1[CH:44]=[CH:43][C:6]([CH2:7][C:8]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:42])([F:41])[P:37]([OH:40])([OH:39])=[O:38])=[CH:32][CH:31]=2)([C:19]([O:21]CC2C=CC=CC=2)=[O:20])[C:9]([O:11]CC2C=CC=CC=2)=[O:10])=[CH:5][CH:4]=1>C(O)=O.CO.Cl[Pd]Cl>[F:42][C:36]([F:41])([P:37]([OH:40])([OH:39])=[O:38])[C:33]1[CH:34]=[CH:35][C:30]([CH2:29][C:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:49])[P:45]([OH:48])([OH:47])=[O:46])=[CH:44][CH:43]=2)([C:19]([OH:21])=[O:20])[C:9]([OH:11])=[O:10])=[CH:31][CH:32]=1

Participants

5

Reactant 1

HCID 154858912,2-Di{4-[difluoro(phosphono)methyl]benzyl}malonic acid, dibenzyl ester

Product 1

HCID 212656882,2-Di{4-[Difluoro(Phosphono)Methyl]Benzyl}Malonic AcidYield 66.6%

Reagents, catalysts & solvents 3

HCID 284Formic AcidCatalystHCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product of Example 2 (0.2 g), PdCl2 and a few drops of HCO2H in 20 mL of MeOH was shaken under 50 psi of H2 for 24 h. The reaction mixture was filtered through celite and the filtrate was concentrated. The residue was lyopholized to give 0.1 g of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-652f38ba5d8c4e6db5c507ec144e985d
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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