BIS(4-METHOXYPHENYL)PHENYLPHOSPHINE OXIDE synthesis
- Product Name:BIS(4-METHOXYPHENYL)PHENYLPHOSPHINE OXIDE
- CAS Number:799-55-3
- Molecular formula:C20H19O3P
- Molecular Weight:338.34
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Yield:799-55-3 98%
Reaction Conditions:
Stage #1: chlorobis(4-methoxyphenyl)phosphane;phenylmagnesium chloride in tetrahydrofuran;diethyl ether at -78 - 20; for 18.5 h;Inert atmosphere;
Stage #2: with dihydrogen peroxide in water;acetone at 20; for 0.25 h;Inert atmosphere;
Steps:
S1 Bis(4-methoxyphenyl)(phenyl)phosphine oxide
Adapted from the procedure of Sinou et al. S2 THF (50 mL, stored over activated 3 ? molecular sieves for 24 h) was added to a flame-dried flask under an atmosphere of Ar. Di-(4-methoxyphenyl)chlorophosphine (4.8 g, 17.1 mmol) was added, and the reaction cooled to- 78 °C. PhMgBr (11.4 mL, 3M in Et2O, 34.2 mmol, 2 eq.) was added over 2.5 h with vigorous stirring. The reaction was warmed to r.t. and stirred for 16 h, before being cooled to 0 °C and quenched with MeOH (10 mL). The solvent was removed under reduced pressure and the crude product filtered through a plug of silica, eluting with EtOAc. Solvent was removed from the eluent under reduced pressure. The residue was taken up in acetone (400 mL) and stirredat r.t.. H2O2 (70 mL, 10% in H2O) was added slowly and the reaction stirred for 15 min before the solvent volume was reduced to c. 100 mL under reduced pressure. The reaction was partitioned between EtOAc (300 mL) and NaCl(sat) (300 mL), and the aqueous phase washed with EtOAc (2 × 200 mL). The combined organic phases were dried over MgSO4, filtered, and the solvent removed under reduced pressure. The residue was purified by flash column chromatography (1:3 EtOAc:PE) to furnish S1 (5.67 g, 16.8 mmol, 98%) as a pale yellow oil
References:
McTernan, Charlie T.;De Bo, Guillaume;Leigh, David A. [Chem,2020,vol. 6,# 11,p. 2964 - 2973] Location in patent:supporting information
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