Water → Benzene, 1,2-dichloro-4-(4-(phenylsulfonyl)phenoxy)-

HRID 1702817Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].[C:12]1([S:18]([C:21]2[CH:26]=[CH:25][C:24](F)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CS(C)=O>[C:12]1([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 9.0 g (0.0550 mole) of 3,4-dichlorophenol dissolved in 150 ml of DMSO was added 2.20 g (0.0550 mole) of NaOH. The mixture was heated to 60° C. and 12.5 g (0.0529 mole) of 4-fluorophenyl phenyl sulfone was added. The reaction mixture was heated at 125° C. for 3.25 hrs and cooled. The mixture was poured into a solution of 100 ml of 20% aqueous NaOH and 600 ml of water. The crystalline product was collected by filtration, washed well with water and partially dried. Recrystallization from ethanol afforded 16.9 g (84.5% yield) of purified 4-(4-(phenylsulfonyl)phenoxy)-1,2-dichlorobenzene, mp 145°-146° C.

Workup

temperatureThe reaction mixture was heated at 125° C. for 3.25 hrs
temperaturecooled
filtrationThe crystalline product was collected by filtration
washwashed well with water
custompartially dried
customRecrystallization from ethanol

Sources & evidence

ORD record: ord-6fa5a2522cec48eeb9116d0a6425c9c2
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04349568

Reaction notes

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