Chemical Properties
clear colorless to light yellow liquid
Uses
Ethyl diphenylphosphinite is used in the synthesis of phosphoramides.
reaction suitability
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
Synthesis
Example 2: 330 g (7.17 mol) of anhydrous ethanol was cooled to -15°C under nitrogen protection. Subsequently, 18 g (1.06 mol) of ammonia was passed at this temperature. Next, 200 g (0.907 mol) of diphenylphosphonium chloride was slowly added dropwise over a period of 1 hour. After the dropwise addition was completed, the reaction mixture was gradually warmed to room temperature with stirring and stirring was continued for 3.5 hours. After completion of the reaction, the mixture was cooled, diafiltrated and the solids were washed with ethanol. The filtrate was treated to ensure that it was free of ethanol and residual ammonia. A small amount of precipitate was removed by filtration through glass material. Finally, purification by thin film distillation at a bath temperature of 140 °C and pressure of 0.3 mbar gave 172 g of ethoxydiphenylphosphine in 83% yield of the theoretical value.
References
[1] Patent: US5705669, 1998, A
[2] J. Gen. Chem. USSR (Engl. Transl.), 1961, vol. 31, p. 2214 - 2217