P,P-Diphenylphosphinic azide → 3,5-Dichloro-4-(4-chlorobenzoyl)benzyl azide

HRID 388760Notes

Reaction equation

HRID 388760 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:5]O.C1(P([N:34]=[N+:35]=[N-:36])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:5][N:34]=[N+:35]=[N-:36]

Participants

4

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 28177663,5-Dichloro-4-(4-chlorobenzoyl)benzyl alcohol

Product 1

HCID 136496623,5-Dichloro-4-(4-chlorobenzoyl)benzyl azide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,5-dichloro-4-(4-chlorobenzoyl)benzyl alcohol (858.B) (1 mole) is reacted with diphenylphosphoryl azide (diphenylphosphonic azide) (DPPA) (1.2 mole, and 1,8-Diazabicyclo[5.4.0]undec-7-ene, (Synonym: DBU) (1.2 mole)) in toluene at cold temperature, followed by aqueous work-up and alcohol titration, to give 3,5-dichloro-4-(4′-chlorobenzoyl)benzyl azide (858.D). DPPA is an organic compound that is used in the synthesis of other organic compounds. Aust. J. Chem 26:1591-1593 (1973). The stability of DPPA towards heating is shown by its distillation at 157° C. and by the fact that vigorous evolution of nitrogen is not observed until a temperature of 175° C. is reached.

Sources & evidence

ORD record
ord-e9a35f1a6848451e97e9fdfbf49dcdc0
Source dataset
uspto-grants-2013_02
Patent number
US08377973B2

Reaction notes

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