Hydrochloric Acid → (2-Nitro-phenylethynyl)-phosphonic acid diethyl ester

HRID 1642067Notes

Reaction equation

HRID 1642067 reaction equation
[CH2:1]([O:3][P:4]([C:9]#[CH:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].C(NC(C)C)(C)C.Cl>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.CCOC(C)=O>[CH2:1]([O:3][P:4]([C:9]#[C:10][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 69115o-IodonitrobenzeneHCID 2784295Diethyl ethynylphosphonate

Product 1

HCID 86638334(2-Nitro-phenylethynyl)-phosphonic acid diethyl ester

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 300 mg of ethynyl-phosphonic acid diethyl ester, 494 mg of 1-iodo-2-nitrobenzene and 0.28 ml of di-isopropylamine in 15 ml THF are sequentially added 43 mg of bis-(triphenylphosphin)-palladium(II)-dichloride and 12 mg of copper(I)iodide and the mixture obtained is refluxed for approximately 2 hours. Following an acidic work-up (1N aqueous HCl and EtOAc) and subsequent column chromatography (2-nitro-phenylethynyl)-phosphonic acid diethyl ester is obtained in the form of a slightly brownish oil.

Workup

  1. customthe mixture obtained
  2. temperatureis refluxed for approximately 2 hours

Sources & evidence

ORD record
ord-f2dd420978b5476eb0aa2aceba494056
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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