Sodium Iodide → Bis(diphenylphosphine)methane monooxide

참여 물질

반응 단계

A mixture of palladium acetate (5 mg; 2.2×10-2 mmol), dppm (2.00 g; 5.21 mmol), 1,2-dibromoethane (2.0 g; 10.64 mmol), and dichloromethane (10 mL) was stirred for 20 minutes. To this solution, aqueous NaOH (20% by weight; 6 mL) containing NaI (40 mg; 0.27 mmol) was added and the mixture was vigorously stirred under reflux for 4 hours. The organic phase was filtered through a silica plug which was then washed with CH2Cl2 /AcOEt (3:1 by volume). The combined organic solutions were evaporated to dryness. The solid residue was dissolved in the minimum amount of boiling CH2Cl2, the warm solution was treated with ether (100 mL; portionwise) and left at room temperature for 2 hours. Slightly yellowish fluffy needles of spectroscopically and TLC pure dppmO were separated, washed with ether, and dried under vacuum. The yield was 1.53 g (74%). 1H NMR (CDCl3, 20° C.), δ: 3.1 (d, 2H, J=12.7 Hz, CH2); 7.1-7.9 (m, 20H, Ph). 31P NMR (CDCl3, 20° C.), δ: -26.5 (d, 1P, JP-P =50.5 Hz, PPh2); 29.8 (d, 1P, JP-P =50.5 Hz, P(O)Ph2).

출처 및 근거