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]([Br:17])[CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:18].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Cl)=[CH:22][N:21]=1>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][O:18][C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=3)=[CH:9][C:4]=2[Cl:3])=[CH:22][N:21]=1Participants
Procedure
To a solution of 0.07 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there is added dropwise a solution of 0.50 g of 2-chloro-4-(3-bromophenoxy)phenol in 3 ml of N,N-dimethylformamide with stirring and ice-cooling. After 30 minutes, a solution of 0.27 g of 2-chloro-5-chloromethylpyridine in 5 ml of N,N-dimethylformamide is added thereto at room temperature, followed by stirring at the same temperature for 10 hours. The reaction mixture is poured into ice-water and extracted twice with 100 ml of ethyl acetate. The extracts are combined together, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel chromatography to give 2-chloro-5-[4-(3-bromophenoxy)-2-chlorophenoxy]methylpyridine.
Workup
- temperatureice-cooling
- customat room temperature
- stirringby stirring at the same temperature for 10 hours
- extractionextracted twice with 100 ml of ethyl acetate
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5d68f6afdf58464f9d7bf02bfb434fb0
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05151428
Linked notes
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