Dimethylformamide → 2',4'-Difluorobiphenylsulfonyl chloride

HRID 221389Notes

Reaction equation

HRID 221389 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-sulfonic 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 was heated at reflux for a further 4 hours. The reaction was then cooled and 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 was heated
  4. temperatureat reflux for a further 4 hours
  5. temperatureThe reaction 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-577ca5ce3534461c8ac77e2a5a07172d
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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