Sodium Sulfite → TetraiSopropyl (chloromethylene)bis(phosphonate)

HRID 1492906Notes

Reaction equation

HRID 1492906 reaction equation
[Cl:1][C:2](Cl)([P:13](=[O:22])([O:18][CH:19]([CH3:21])[CH3:20])[O:14][CH:15]([CH3:17])[CH3:16])[P:3](=[O:12])([O:8][CH:9]([CH3:11])[CH3:10])[O:4][CH:5]([CH3:7])[CH3:6].S([O-])([O-])=O.[Na+].[Na+]>C(O)C.O>[Cl:1][CH:2]([P:3](=[O:12])([O:4][CH:5]([CH3:7])[CH3:6])[O:8][CH:9]([CH3:11])[CH3:10])[P:13](=[O:22])([O:18][CH:19]([CH3:20])[CH3:21])[O:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 41937482-((Dichloro-di(propan-2-yloxy)phosphorylmethyl)-propan-2-yloxyphosphoryl)oxypropane

Product 1

HCID 13479864TetraiSopropyl (chloromethylene)bis(phosphonate)

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Into a solution containing 8.2 g (0.02 moles) of tetraisopropyl (dichloromethylene)bisphosphonate in 70 ml of ethanol, 9.0 g of sodium sulphite in 250 ml of water are added while stirring during 15 minutes at 10° to 15° C., whereafter the mixture is stirred for 1 h. The mixture is extracted with chloroform and the extract is dried (MgSO4) and filtered. The filtrate is evaporated under a vacuum, whereby about 7.6 g (100% of the theor.) of tetraisopropyl (monochloromethylene)bisphosphonate (31P-NMR (CDCl3 : δ 12.04 ppm) are obtained as a colourless oil, at a concentration of 98%.

Workup

  1. additionare added
  2. stirringis stirred for 1 h
  3. extractionThe mixture is extracted with chloroform
  4. dry with materialthe extract is dried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate is evaporated under a vacuum, whereby about 7.6 g (100% of the theor

Sources & evidence

ORD record
ord-a154b0c6eec747718c9077029962df67
Source dataset
uspto-grants-1994_12
Patent number
US05376649

Reaction notes

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