Dimethylformamide → 2',4'-Difluorobiphenylsulfonyl chloride

HRID 2170021Notes

Reaction equation

HRID 2170021 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][C:12](S(O)(=O)=O)=[CH:11][CH:10]=1.CN(C=[O:23])C.[S:24]([Cl:27])(Cl)=[O:25]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([S:24]([Cl:27])(=[O:25])=[O:23])=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 866551792',4'-Difluorobiphenyl-4-sulfonic acid

Product 1

HCID 866551802',4'-Difluorobiphenylsulfonyl chloride

Procedure

2′,4′-Difluorobiphenyl-4-sulphonic acid (12.1 g, 47 mmol) was suspended in thionyl chloride (100 mL). The mixture was heated at reflux for 30 minutes, when a catalytic amount of dry DMF was added and the reaction mixture was heated at reflux for a further 4 hours. The reaction mixture was then cooled, the thionyl chloride evaporated and the residue was then azeotroped with toluene (3×10 mL). The resulting yellow/orange gum was taken up into EtOAc (250 mL) and washed with water (50 mL) and brine (50 mL), and dried over MgSO4. Filtration and evaporation gave the title compound as a brown oil which crystallized on standing (11 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for a further 4 hours
  5. temperatureThe reaction mixture was then cooled
  6. customthe thionyl chloride evaporated
  7. customthe residue was then azeotroped with toluene (3×10 mL)
  8. washwashed with water (50 mL) and brine (50 mL)
  9. dry with materialdried over MgSO4
  10. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-a37332c8ab8149f096f111a8ef09745a
Source dataset
uspto-grants-2015_06
Patent number
US09050329B1

Reaction notes

Loading…