Phosphorus pentachloride → HCID 54323173, compound

HRID 2393232Notes

Reaction equation

HRID 2393232 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][P:11](=[O:18])(OCC)[O:12][CH2:13][CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][P:11]([Cl:20])(=[O:18])[O:12][CH2:13][CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 256065Diethyl 4-nitrobenzylphosphonate

Product 1

HCID 54323173HCID 54323173, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

This method is a modification of that outlined by Doak and Freedman (Ref. 178). Diethyl (p-nitrophenyl)methylphosphonate (7.16) (1.0 g, 3.6 mmol) in DCM (10 ml) was added dropwise to a solution of PCl5 (0.9 g, 4.32 mmol) in CCl4 (20 ml) under an inert atmosphere. The reaction was stirred at 30° C. and the progress of the chlorination was followed by 31P NMR which showed the reaction was complete after 24 h. Solvent and phosphoryl chloride were removed in vacuo to yield a pale yellow, moisture-sensitive oil (0.8 g, 90%) which was used without further purification. δH (250 MHz, CDCl3) 1.40 (3H, t, J 7.5 Hz, CH3), 3.60 (2H, d, 2JPH 22.5 Hz, Ar--CH2), 4.25-4.43 (2H, m, JHP 8.5 Hz, J 7.5 Hz,CH2), 7.5 (2H, d, J 7.5 Hz, Ar--H), 8.20 (2H, d, J 7.5 Hz, Ar--H); δP (101 MHz, CDCl3) 35.94 (s).

Workup

  1. customSolvent and phosphoryl chloride were removed in vacuo

Sources & evidence

ORD record
ord-a4a50fd528cf402dbdd3e7982b15363d
Source dataset
uspto-grants-1998_09
Patent number
US05807688

Reaction notes

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