3,4-Dichlorophenol → Benzene, 1,2-dichloro-4-(4-((trifluoromethyl)sulfonyl)phenoxy)-

HRID 2164645Notes

Reaction equation

HRID 2164645 reaction equation
[F:1][C:2]([S:5]([C:8]1[CH:13]=[CH:12][C:11](Cl)=[CH:10][CH:9]=1)(=[O:7])=[O:6])([F:4])[F:3].[Cl:15][C:16]1[CH:17]=[C:18]([OH:23])[CH:19]=[CH:20][C:21]=1[Cl:22].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[F:1][C:2]([F:4])([F:3])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:23][C:18]2[CH:19]=[CH:20][C:21]([Cl:22])=[C:16]([Cl:15])[CH:17]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 7033241-Chloro-4-(trifluoromethylsulfonyl)benzene

Product 1

HCID 514861Benzene, 1,2-dichloro-4-(4-((trifluoromethyl)sulfonyl)phenoxy)-Yield 86.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 4.7 g (0.0192 mole) of 4-chlorophenyl trifluoromethyl sulfone prepared according to known procedures (see E. A. Nodiff et al., J. Org. Chem., 25, 60 (1959)) and 4.7 g (0.0288 mole) of 3,4-dichlorophenol dissolved in 150 ml of DMSO was added 4.0 g (0.0288 mole) of K2CO3. The reaction mixture was heated at 125° C. for 3.5 hrs and the product recovered (6.15 g, 86.3% yield) as described in Example 18. Recrystallization from ethanol afforded purified 4-(4-((trifluoromethyl)sulfonyl)phenoxy)-1,2-dichlorobenzene, mp 77°-78° C.

Workup

  1. customthe product recovered (6.15 g, 86.3% yield)
  2. customRecrystallization from ethanol
  3. customafforded
  4. custompurified 4-(4-((trifluoromethyl)sulfonyl)phenoxy)-1,2-dichlorobenzene, mp 77°-78° C.

Sources & evidence

ORD record
ord-e79f6e3caa6c4905ab900af12613a754
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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