Chlorosulfonic acid → 2',4'-Difluorobiphenyl sulfonic acid

HRID 221388Notes

Reaction equation

HRID 221388 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[S:16]([OH:19])(=[O:18])=[O:17]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1699742,4-Difluoro-1,1'-biphenyl

Product 1

HCID 866562612',4'-Difluorobiphenyl sulfonic acidYield 40.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2,4-Difluorobiphenyl (21.2 g, 111 mmol) was dissolved in chloroform (120 mL) and chlorosulfonic acid (12.5 mL, 188 mmol) was added dropwise. The reagents were stirred overnight at room temperature. The reaction was concentrated in vacuo and the residue was taken up into EtOAc (100 mL) and washed with water (3×25 mL). The organics were shaken with brine, whereupon a flocculent solid formed. This was filtered and washed with EtOAc and dried to give 2′,4′-difluorobiphenyl sulfonic acid as an off-white solid (12.1 g).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washwashed with water (3×25 mL)
  3. stirringThe organics were shaken with brine, whereupon a flocculent solid
  4. customformed
  5. filtrationThis was filtered
  6. washwashed with EtOAc
  7. customdried

Sources & evidence

ORD record
ord-2569bbcb7a4044d7bbd393c807fd2e91
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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