Reaktion #360854

Reaktionsgleichung

4,4'-sulfonyldiphenol

diphenylphosphinyl chloride

→

title compound

Ausbeute 94.0%

Bis[4-(diphenylphosphinyloxy)phenyl] Sulfone

Ausbeute 94.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser
2. 2
   TemperaturThe resulting mixture was heated
3. 3
   Temperaturat reflux for 7 hours
4. 4
   SonstigeAfter completion of the reaction
5. 5
   Sonstigethe mixture was partitioned between water (100 mL) and CH2Cl2 -Et2O (1:3; 400 mL)
6. 6
   Waschenthe organic phase was washed successively with 50 mL portions of 5 percent NaOH, water, 5 percent HCl, water and brine
7. 7
   Trocknenit was dried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigeleaving a white solid residue
11. 11
    SonstigeRecrystallization from ethyl acetate-THF (9:1)

Vorschrift

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.

Quelle