反応 #360852

反応方程式

4-phenoxyphenol

benzenephosphonothioic dichloride

→

title compound

収率 79.0%

Bis(4-phenoxyphenyl) Benzenephosphonothioate

収率 79.0%

溶媒

pyridine

反応条件

後処理

1. 1
   その他An oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser
2. 2
   温度was heated
3. 3
   温度at reflux for 1 hour
4. 4
   温度to cool
5. 5
   その他of partitioning the reaction mixture between CH2Cl2 (100 mL) and water (100 mL)
6. 6
   洗浄washing the organic phase successively with 100 mL portions of 5 percent NaOH, water, 5 percent HCl, water, and saturated brine
7. 7
   その他Drying
8. 8
   ろ過(MgSO4) filtration and concentration
9. 9
   その他gave a red oily residue
10. 10
    その他Purification by chromatography on flash-grade silica gel (4"×2" i.d.)
11. 11
    洗浄eluting with CH2Cl2

実験手順

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-phenoxyphenol (8.64 g, 46.4 mmol), 4-dimethylaminopyridine (0.57 g, 4.7 mmol), and anhydrous pyridine (40 mL), and the stirred solution was treated slowly with benzenephosphonothioic dichloride (3.6 mL, 23.2 mmol) via syringe. The resulting mixture was stirred at ambient temperature for 64 hours, then was heated at reflux for 1 hour, and allowed to cool. The reaction was monitored periodically by HPLC. Workup consisted of partitioning the reaction mixture between CH2Cl2 (100 mL) and water (100 mL), then washing the organic phase successively with 100 mL portions of 5 percent NaOH, water, 5 percent HCl, water, and saturated brine. Drying (MgSO4) filtration and concentration gave a red oily residue. Purification by chromatography on flash-grade silica gel (4"×2" i.d.), eluting with CH2Cl2 , afforded 9.3 g (79 percent yield) of the title compound as a yellow, viscous oil which had a PDSC (O2) onset/extrap (° C.) of 248/324.

出典