Sodium hydride → 2-Chloro-5-[2-chloro-4-(3-trifluoromethylphenoxy)phenoxy]methylpyridine

HRID 5205

Reaktionsgleichung

Reaktionsgleichung von HRID 5205
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:21].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Cl)=[CH:25][N:24]=1>CN(C)C=O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][O:21][C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=3)=[CH:9][C:4]=2[Cl:3])=[CH:25][N:24]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 189667272-Chloro-4-(3-trifluoromethylphenoxy)phenol

Produkt 1

HCID 197980992-Chloro-5-[2-chloro-4-(3-trifluoromethylphenoxy)phenoxy]methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a solution 0.07 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there was added dropwise a solution of 0.50 g of 2-chloro-4-(3-trifluoromethylphenoxy)phenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 30 minutes, a solution of 0.28 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, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 2-chloro-5-[2-chloro-4-(3-trifluoromethylphenoxy)phenoxy]methylpyridine.

Aufarbeitung

  1. temperatureice-cooling
  2. customat room temperature
  3. stirringby stirring at the same temperature for 10 hours
  4. extractionextracted twice with 100 ml of ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cfef7c7616f74cf4b1c7989b7ccd6e17
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243087

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