Oxalyl chloride → HCID 54323173, compound

HRID 1517233Notes

Reaction equation

HRID 1517233 reaction equation
C(Cl)(=O)C([Cl:4])=O.[N+:7]([C:10]1[CH:24]=[CH:23][C:13]([CH2:14][P:15](=O)([O:19]CC)[O:16][CH2:17][CH3:18])=[CH:12][CH:11]=1)([O-:9])=[O:8]>C(Cl)Cl.C(Cl)(Cl)Cl>[N+:7]([C:10]1[CH:24]=[CH:23][C:13]([CH2:14][P:15]([Cl:4])(=[O:19])[O:16][CH2:17][CH3:18])=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 256065Diethyl 4-nitrobenzylphosphonate

Product 1

HCID 54323173HCID 54323173, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.8 mL, 9.6 mmol, 2 M solution in methylene chloride) was added to a solution of diethyl 4-nitrobenzylphosphonate 298 (546 mg, 2.0 mmol) in methylene chloride (10 mL) at room temperature under nitrogen, and the mixture was stirred for 48 h. The mixture was diluted with chloroform (10 mL), and the solvent was concentrated to provide 520 mg (99% yield) of ethyl 4-nitrobenzylphosphonochloridate 299 as a thick yellow oil that was used in the next step without purification.

Workup

  1. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-e59de9d76c504ad885b6b7fdc2a45f4f
Source dataset
uspto-grants-2012_07
Patent number
US08232274B2

Reaction notes

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