Benzyl Bromide → 1-(Benzylsulfonyl)-4-bromo-2-chlorobenzene

HRID 70578Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:24]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[Cl:12])(=[O:10])=[O:9])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-bromo-2-chlorobenzenesulfonyl chloride (1.16 g), sodium sulfite (1.01 g) and sodium bicarbonate (672 mg) in water (8 mL) was stirred at 100° C. for 1.5 hours. The reaction solution was cooled to 50° C. and tetrabutylammonium bromide (1.29 g) and benzyl bromide (1.43 mL) were added, after which the mixture was stirred at 70° C. for further three hours. The reaction solution was cooled to room temperature and water was added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the title compound as a white solid (1.29 g, 94%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionfollowed by extraction with chloroform
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-79a6fae59ea343e4a8161c43b77776bf
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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