1-Chloro-4-(methylsulfonyl)benzene → Benzene, 1-bromo-4-(4-(methylsulfonyl)phenoxy)-

HRID 2164632Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 9.54 g (0.0500 mole) of 4-chlorophenyl methyl sulfone, 13.0 g (0.0750 mole) of 4-bromophenol, 10.37 g (0.0750 mole) of K2CO3 and 150 ml of sulfolane was heated at 150° C. for 5.5 hrs and at 160° C. for 3.5 hrs. The reaction mixture was cooled and poured into a solution of 200 ml of 20% aqueous NaOH and 400 ml of water. The crystalline product was collected by filtration, washed well with water and dried, which gave 8.27 g (50.6% yield) of product. Recrystallization from ethanol afforded purified 1-bromo-4-(4-(methylsulfonyl)phenoxy)benzene, mp 127.5°-129° C.

Workup

temperatureThe reaction mixture was cooled
filtrationThe crystalline product was collected by filtration
washwashed well with water
customdried

Sources & evidence

ORD record: ord-52776baa96cc472489d1e828c8b43268
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04505929

Reaction notes

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