4-Bromobiphenyl → 4-BROMO-4'-SULFOBIPHENYL

HRID 1292243Notes

Reaction equation

HRID 1292243 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[S:15]([OH:18])(=[O:17])=[O:16]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 71014-BromobiphenylHCID 24638Chlorosulfonic acid

Product 1

HCID 45247074-BROMO-4'-SULFOBIPHENYLYield 79.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4-bromobiphenyl (50 g, 0.21 mol) in chloroform (200 mL) was added dropwise at room temperature chlorosulfonic acid (32.5 g, 0.28 mol). The solution was stirred at room temperature for 16 hours, then diluted with hexanes (200 mL). The precipitate was collected by filtration and washed with hexanes to give 4'-bromobiphenyl-4-sulfonic acid (52.3 g, 79%) as a white solid. The crude product was used in the next step without further characterization.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with hexanes

Sources & evidence

ORD record
ord-a769a92bc2f64a84af08b23594258d81
Source dataset
uspto-grants-1998_05
Patent number
US05756545

Reaction notes

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