[1] Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds. J. Org. Chem. 2020, 85, 22, 14653–14663.
A dried 250 mL flask was charge with p-tolylmagnesium bromide (33 mmol, 1.0 mol/L in THF) in an ice-water bath under N2. A solution of diethylphosphite (1.3 mL, 10.0 mmol) in anhydrous THF (5.0 mL) was then added dropwise over 30 min. The mixture was further stirred at ambient temperature overnight. After that, the reaction mixture was cooled to 0 °C again, and HCl (100 mL 0.1 N) was added dropwise. The mixture was extracted with dichloromethane (100 mL × 3), and the combined organic phase was washed with saturated NaCl solution, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc) to give the desired product BIS(P-TOLYL)PHOSPHINE OXIDE.
