3,4-Dichlorobenzotrifluoride → 3-(2'-Chloro-4-trifluoromethylphenoxy)-6-chlorothioanisole

HRID 1702740Notes

Reaction equation

HRID 1702740 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[S:9][CH3:10].[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][C:17]=1Cl.[OH-].[Na+]>CS(C)=O>[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:15]=[CH:16][C:17]=1[O:8][C:5]1[CH:4]=[C:3]([S:9][CH3:10])[C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 94813,4-DichlorobenzotrifluorideHCID 14798Sodium HydroxideHCID 218771864-Chloro-3-(methylthio)phenol

Product 1

HCID 205247373-(2'-Chloro-4-trifluoromethylphenoxy)-6-chlorothioanisoleYield 80.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

50 g of 4-chloro-3-methylmercaptophenol, 62 g of 3,4-dichlorobenzotrifluoride and 12 g of sodium hydroxide are stirred in 150 ml of dimethyl sulphoxide for 6 hours at 142° C. The reaction mixture is then poured onto ice and extracted with toluene. Distillation of the organic phase yields 81 g of 3-(2'-chloro-4-trifluoromethylphenoxy)-6-chlorothioanisole with a boiling point of 158° C./0.4 mbar.

Workup

  1. additionThe reaction mixture is then poured onto ice
  2. extractionextracted with toluene
  3. distillationDistillation of the organic phase

Sources & evidence

ORD record
ord-b17eee9299504d18a4c2c398e032ba2d
Source dataset
uspto-grants-1982_09
Patent number
US04349377

Reaction notes

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