[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[CH:16][C:17]=1[Cl:18].C([O-])([O-])=O.[K+].[K+].S1(CCCC1)(=O)=O.[OH-].[Na+]>O>[Cl:18][C:17]1[CH:16]=[CH:15][C:14]([O:19][C:7]2[CH:8]=[CH:9][C:4]([S:2]([CH3:1])=[O:3])=[CH:5][CH:6]=2)=[CH:13][C:12]=1[Cl:11]
A mixture of 16.14 g (0.102 mole) of 4-fluorophenyl methyl sulfoxide, 33.18 g (0.204 mole) of 3,4-dichlorophenol, 28.15 g (0.204 mole) of anhydrous K2CO3 and 150 ml of sulfolane was heated at 170° C. for 4 hrs and cooled. The reaction mixture was poured into a solution of 20% aqueous NaOH and 500 ml of water. The homogeneous solution was extracted with diethyl ether. The organic layer was washed with water, dried (Na2SO4) and solvent removed in vacuo leaving 24.5 g (79.8% yield) of product. Recrystallization from ethanol followed by column chromatography using silica gel as the support and chloroform as the eluent afforded purified 1,2-dichloro-4-(4-(methylsulfinyl)phenoxy)benzene, mp 92°-93.5° C.
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