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

HRID 252430Notes

Reaction equation

HRID 252430 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 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 500 mL round-bottom-flask equipped with an addition funnel, stirring bar, and gas inlet was charged with 4-bromo-biphenyl (50 g, 0.215 mol) and chloroform (200 mL) then purged with nitrogen. Chlorosulfonic acid (18 mL, 0.27 mol) was added dropwise to the solution from the addition funnel then stirred for 1 hour. The resulting precipitate was collected by vacuum filtration, washed with cold chloroform, and dried under vacuum to give 61.97 g of 4′-bromo-biphenyl-4-sulfonic acid (92% yield).

Workup

  1. customA 500 mL round-bottom-flask equipped with an addition funnel
  2. customthen purged with nitrogen
  3. stirringthen stirred for 1 hour
  4. filtrationThe resulting precipitate was collected by vacuum filtration
  5. washwashed with cold chloroform
  6. customdried under vacuum

Sources & evidence

ORD record
ord-8d95b9619dcc40e9810898c9e6d4841e
Source dataset
uspto-grants-2011_01
Patent number
US07868086B2

Reaction notes

Loading…