3,4-Dichlorophenol → 1,2-Dichloro-4-(3-methyl-4-(methylsulfonyl)phenoxy)benzene

HRID 2164640Notes

Reaction equation

HRID 2164640 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][C:6]=1[CH3:12])(=[O:4])=[O:3].[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].C([O-])([O-])=O.[K+].[K+]>S1(CCCC1)(=O)=O>[CH3:12][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:5]=1[S:2]([CH3:1])(=[O:4])=[O:3])[O:21][C:16]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=1

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 204050994-Chloro-2-methyl-1-(methylsulfonyl)benzene

Product 1

HCID 5148731,2-Dichloro-4-(3-methyl-4-(methylsulfonyl)phenoxy)benzeneYield 63.4%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A slurry of 6.14 g of 4-chloro-2-methylphenyl methyl sulfone, 8.35 g of 3,4-dichlorophenol and 7.08 g of K2CO3 in 150 ml of sulfolane was heated at 170° C. for 7 hrs. The product (6.3 g, 63.4% yield) was isolated from the reaction mixture essentially as described in Example 18. Recrystallization from ethanol afforded purified 4-(3-methyl-4-(methylsulfonyl)phenoxy)-1,2-dichlorobenzene, mp 154°-156° C.

Sources & evidence

ORD record
ord-eb3fc38cb41b4e1cb7a4a638628381e2
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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