Triethyl phosphite → Diethyl (2-nitrophenyl)phosphonate

HRID 1642068Notes

Reaction equation

HRID 1642068 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([O:13][P:14]([O:18]CC)[O:15][CH2:16][CH3:17])[CH3:12]>CCO.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:11]([O:13][P:14]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])(=[O:18])[O:15][CH2:16][CH3:17])[CH3:12]

Participants

5

Reactant 2

HCID 31215Triethyl phosphiteHCID 69115o-Iodonitrobenzene

Product 1

HCID 12547206Diethyl (2-nitrophenyl)phosphonate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 702EthanolSolvent

Procedure

3.9 g of Cu(II) acetate are added to a solution of 5 g 1-iodo-2-nitrobenzene and 5 g of triethylphosphite in 20 ml of EtOH, the mixture obtained is refluxed for 24 hours, cooled to rt and partitioned between EtOAc and half-saturated aqueous NaCl-solution. The organic layer obtained is dried, solvent is evaporeated and the evaporation residue is subjected to column chromatography (silicagel, toluene:acetonitrile=3:1). (2-Nitro-phenyl)-phosphonic acid diethyl ester is obtained in the form of an orange oil. MS: MNa+ 282

Workup

  1. customthe mixture obtained
  2. temperatureis refluxed for 24 hours
  3. custompartitioned between EtOAc and half-saturated aqueous NaCl-solution
  4. customThe organic layer obtained
  5. customis dried

Sources & evidence

ORD record
ord-7340998abfa942cb96692f7ad97fe9a8
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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