反应详情

An oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser carrying a CaCl2 -Drierite drying tube, and a heating mantle, was charged with 4,4'-sulfonyldiphenol (3.9 g, 15.6 mmol), 4-dimethylaminopyridine (0.39 g, 3.2 mmol), and anhydrous pyridine (35 mL), and the stirred solution was treated slowly with diphenylphosphinyl chloride (6.5 mL, 34.1 mmol) via syringe. The resulting mixture was heated at reflux for 7 hours, then was allowed to stand at room temperature for 16 hours. The reaction was monitored periodically by HPLC. After completion of the reaction, the mixture was partitioned between water (100 mL) and CH2Cl2 -Et2O (1:3; 400 mL), and the organic phase was washed successively with 50 mL portions of 5 percent NaOH, water, 5 percent HCl, water and brine, then it was dried (MgSO4), filtered and concentrated leaving a white solid residue. Recrystallization from ethyl acetate-THF (9:1) afforded 9.5 g (94 percent yield) of the title compound as a white fluffy solid, m.p. 210-211° C. which had a PDSC (O2) onset/extrap (° C.) of 376/397.

1. customAn oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser
2. temperatureThe resulting mixture was heated
3. temperatureat reflux for 7 hours
4. customAfter completion of the reaction
5. customthe mixture was partitioned between water (100 mL) and CH2Cl2 -Et2O (1:3; 400 mL)
6. washthe organic phase was washed successively with 50 mL portions of 5 percent NaOH, water, 5 percent HCl, water and brine
7. dry with materialit was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customleaving a white solid residue
11. customRecrystallization from ethyl acetate-THF (9:1)