Reaktion #5300

Reaktionsgleichung

sodium hydride

2-chloro-4-phenoxyphenol

2-chloro-5-chloromethylpyridine

→

2-chloro-5-(2-chloro-4-phenoxyphenoxy)methylpyridine

Ausbeute 70.8%

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturice-cooling
2. 2
   Sonstigeat room temperature
3. 3
   workup.STIRRINGby stirring at the same temperature for 10 hours
4. 4
   Extraktionextracted twice with 100 ml of ethyl acetate
5. 5
   Waschenwashed with water
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of 0.09 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there was added dropwise a solution of 0.45 g of 2-chloro-4-phenoxyphenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 30 minutes, a solution of 0.34 g of 2-chloro-5-chloromethylpyridine in 5 ml of N,N-dimethylformamide was added thereto at room temperature, followed by stirring at the same temperature for 10 hours. The reaction mixture was poured into ice-water and extracted twice with 100 ml of ethyl acetate. The extracts were combined together, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 0.50 g of 2-chloro-5-(2-chloro-4-phenoxyphenoxy)methylpyridine. Yield, 71%. nD22 : 1.6173

Quelle