Water → 3-Chloro-2-[4-chloro-2-fluoro-5-(methylthiomethoxy)phenyl]-5-trifluoromethylpyridine

HRID 1870710Notes

Reaction equation

HRID 1870710 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=2)=[CH:6][C:5]=1[OH:22].[CH3:23][S:24][CH2:25]Cl.O>CN(C)C=O>[Cl:17][C:16]1[C:11]([C:7]2[CH:6]=[C:5]([O:22][CH2:23][S:24][CH3:25])[C:4]([Cl:3])=[CH:9][C:8]=2[F:10])=[N:12][CH:13]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 118235682-Chloro-5-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-fluorophenol

Product 1

HCID 186929333-Chloro-2-[4-chloro-2-fluoro-5-(methylthiomethoxy)phenyl]-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.1 g (4.4 mmol) of sodium hydride was added to a solution of 1.3 g (4 mmol) of 2-chloro-5-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-fluorophenol in 50 ml of dimethylformamide. After the mixture has been stirred for 1 hour, it was treated with 0.5 g (5.2 mmol) of methylthiomethyl chloride. Then, the mixture was stirred for another hour. For working-up, the reaction mixture was treated with 50 ml of water. The product was then extracted with 100 ml of methyl tert-butyl ether. The organic phase was dried over magnesium sulfate and finally concentrated. Yield: 0.3 g.

Workup

  1. stirringThen, the mixture was stirred for another hour
  2. extractionThe product was then extracted with 100 ml of methyl tert-butyl ether
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationfinally concentrated

Sources & evidence

ORD record
ord-f0c538e209b042688cb20276eb1c7799
Source dataset
uspto-grants-2000_08
Patent number
US06100218

Reaction notes

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