Trimethyl phosphite → (4-methylsulfanyl-benzyl)-phosphonic acid dimethyl ester

HRID 896668Notes

Reaction equation

HRID 896668 reaction equation
[CH3:1][O:2][P:3]([O:6]C)[O:4][CH3:5].[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1>Cl.C(OCC)(=O)C>[CH3:1][O:2][P:3]([CH2:14][C:13]1[CH:16]=[CH:17][C:10]([S:9][CH3:8])=[CH:11][CH:12]=1)(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 2

HCID 8472Trimethyl phosphiteHCID 701281-(Chloromethyl)-4-(methylthio)benzene

Product 1

HCID 10955842(4-methylsulfanyl-benzyl)-phosphonic acid dimethyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To trimethylphosphite (8.6 g, 70 mmol) at 140° C. was added 4-methylthiobenzyl chloride (10 g, 58 mmol). The resulting mixture was stirred at 140° C. for 18 h, cooled at 21° C. then diluted with HCl 10% and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (eluting with ethyl acetate) provided the (4-methylsulfanyl-benzyl)-phosphonic acid dimethyl ester compound.

Workup

  1. temperaturecooled at 21° C.
  2. washThe organic extracts were washed (H2O), (brine),
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-ea8c3f1807ef4113873d86199ba421d7
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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