ChemicalBook CAS DataBase List DIETHYL PHENYLPHOSPHONATE

DIETHYL PHENYLPHOSPHONATE synthesis

14synthesis methods

Product Name:DIETHYL PHENYLPHOSPHONATE
CAS Number:1754-49-0
Molecular formula:C10H15O3P
Molecular Weight:214.2

A dried 25 mL flask was charge with triethyl phosphite (11.0 mmol, 1.27 mL) and benzoyl chloride (10.0 mmol, 1.72 mL). After the mixture was stirred for 12 h at room temperature, the crude product was purified by column chromatography over silica gel (300–400 mesh) using CH2Cl2 as an eluent to give analytically pure product Diethyl Phenylphosphonate.

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Yield: 89%

Reaction Conditions:

with bis(1,5-cyclooctadiene)nickel ⁽⁰⁾;2-(di-tert-butylphosphaneyl)-4-methoxy-N,N-dimethylaniline;N-ethyl-N,N-diisopropylamine in toluene at 110; for 24 h;Inert atmosphere;Schlenk technique;

Steps:

Ni-Catalyzed cross-coupling of aryl tosylates with H(O)P(OR)2.
General procedure: Under the atmosphere of N2, 0.2 mmol of aryl tosylate 1a, 3 mol % Ni(cod)2, 3 mol % L8, DIPEA (0.6 mmol), and 2 mL of toluene were charged into a 10 mL Schlenk tube, then 0.15 mmol of (i-PrO)2P(O)H (2a) was added to the mixture. The reaction was processed at 110°C for 10 h, then the other 0.15 mmol of (i-PrO)2P(O)H (2a) was added. The mixture was further stirred at 110°C for 14 h. After removal of the volatiles, the residue was passed through a short silica chromatographical column to afford analytically pure organophosphorus compound 3a. Most of thus synthesized products had been reported earlier, and their spectral data matched those presented in literature. The products 3e, 3f, 3n, 3o, 3p', 3r, and 3r' were the newly synthesized compounds.

References:

Li, Chun-jing [Russian Journal of General Chemistry,2020,vol. 90,# 4,p. 725 - 730]

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98-80-6 Synthesis