Diethyl chlorophosphonate

From (IV), chlorosulphonic acid (V) and benzene sulphonic acid (VI) are obtained by the replacement of H by Cl and C6H5 respectively Arguing along similar lines, (VIII) is phosphonic acid and (IX) is fluorophosphonic acid, hence (I) is diethyl chlorophosphonate. Th ... 

Keywords phenol, diethyl chlorophosphonate, magnesia, phosphorylation, aryl diethyl phosphate... 

General Procedure for the Phosphorylation of Phenol with Diethyl Chlorophosphonate on the Surface of Magnesia. Magnesia (0.3 g) was added to a mixture of diethyl chlorophosphonate (0.86 mL, 6 mmol) and the phenol (5 mmol). This mixture was stirred at room temperature or 60 °C for 0.25-1 h. The solid mixture was washed with dichloromethane (4x25 mL). The solution was then washed with a dilute NaOH solution and a saturated sodium chloride solution and dried over MgS04. After evaporating of solvent, the crude product was isolated in a pure state by distillation in vacuo in 85-95% yield. 

The Grignard reagent of a fluorinated aryl bromide on reaction with diethyl chlorophosphonate can lead to the corresponding diethyl arylphosphonatc, e, g. formation of diethyl [3-(trifluoro-methyl)phenyl]phosphonate (30) from bromide 29. ... 

Coupung, dehydrative Bis-o-phenylene pyrophosphite. N,N -Carbonyldiimidazole. N,N -Carbonyl-J-triazine. l-Cyclohexyl-3-(2-morpholinomethyl)-carbodiimide. 1,1-Di-chlorodiethyl ether. Dicyclohexylcarbodiimide. Diethyl chlorophosphonate. Diethyl-cyanamide. Diethyl ethylenepyrophosphite. N-(3-Dimethylaminopropyl)-N -ethylcarbo-diimide hydrochloride. Diphenylketene p-tolylamine. Ethoxyacetylene. l-Ethyl-3(3 -di-methylaminopropyllcarbodiimide hydrochloride. Ethylene chlorophosphite. N-Ethyl-S-phenyliioxazolium-3 -sulfonate. N-Hydropyridine. N-Hydroxyphthalimide. N-Hydroxy-piperidine, N-Hydroxysuccinimide. Phenylphosphorodi-d-imidazolate). 

S0ZC12 added at 35-40° to stirred diethyl phosphite, and stirring continued for 90 min. —> diethyl chlorophosphonate. Y 90%.—CS9 was used as a solvent for the preparation of dibenzyl chlorophosphonate. —With SO CI2 this reaction can be carried out at room temp., while temp, below 0° are necessafy with chlorine. (F. e. s. F. R. Atherton, H. T. Howard, and A. R. Todd, Soc. 1948, 1106.)... 

Arguing along similar lines, (VIII) is phosphonic acid and (IX) is fluorophosphonic acid, hence (I) is diethyl chlorophosphonate. The... 

Diethyl chlorophosphonate, see D-00355 Diethyl cyclohexylboronate, in C-00352 2,13-Diethyldibenzo-18-crown-6, see D-00351 2,19-Diethyldibenzo-30-crown-10, see D-00348 7,18-Diethyldibenzo-18-crown-6, see D-00352... 

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