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

HRID 2170020Notes

Reaction equation

HRID 2170020 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[CH:14]=[CH:13][C:12]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

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

Product 1

HCID 866551792',4'-Difluorobiphenyl-4-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 mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue 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-4-sulfonic acid as an off-white solid (12.1 g).

Workup

  1. concentrationThe reaction mixture 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-e0bc0fe42db744fc96f0d97515051df8
Source dataset
uspto-grants-2015_06
Patent number
US09050329B1

Reaction notes

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