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

HRID 69568

Reaktionsgleichung

Reaktionsgleichung von HRID 69568
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 866551792',4'-Difluorobiphenyl-4-sulfonic acidAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d4c90947511b46f4b333d6a0cdd8281c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822507B2

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