Dimethylformamide → 2',4'-Difluorobiphenylsulfonyl chloride

HRID 623379Notes

Reaction equation

HRID 623379 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-3f3c5b6db6cc4b82bf982f9c31d21d3e
Source dataset
uspto-grants-2016_04
Patent number
US09302984B2

Reaction notes

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