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

HRID 5205

Reaction equation

HRID 5205 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cfef7c7616f74cf4b1c7989b7ccd6e17
Source dataset
uspto-grants-1993_09
Patent number
US05243087

Linked notes

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