Dimethylformamide → 4'-Bromobiphenyl-4-sulfonyl chloride

HRID 252431Notes

Reaction equation

HRID 252431 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](S(O)(=O)=O)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[S:18]([Cl:21])(Cl)=[O:19].CN(C=[O:26])C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:18]([Cl:21])(=[O:19])=[O:26])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86621785HCID 86621785, compound

Product 1

HCID 27568454'-Bromobiphenyl-4-sulfonyl chlorideYield 78%

Procedure

A 500 mL round-bottom-flask equipped with an addition funnel, stirring bar, and gas inlet was charged with the 4-bromo-biphenyl sulfonic acid, DMF (200 mL) then purged with nitrogen. The flask was chilled in an ice-bath and thionyl chloride (45 mL, 0.62 mol) was added dropwise to the solution from the addition funnel. The flask was allowed to warm to room temperature and stirred for 3 hours. The solution was poured into 2 L ice water to precipitate the product, which was collected by vacuum filtration. The solids were dissolved in ether and the solution was dried with magnesium sulfate, filtered, and evaporated on a rotary evaporator. The resulting solids were dried under vacuum to give 59.66 g (84% yield) and recrystallized from hot toluene (100 mL) by adding cyclohexane (250 mL). The crystals were collected, washed with cyclohexane, and dried under vacuum to give 55.20 g of 4′-bromo-biphenyl-4-sulfonyl chloride (78% yield).

Workup

  1. customA 500 mL round-bottom-flask equipped with an addition funnel
  2. customthen purged with nitrogen
  3. temperatureThe flask was chilled in an ice-bath
  4. stirringstirred for 3 hours
  5. customto precipitate the product, which
  6. filtrationwas collected by vacuum filtration
  7. dissolutionThe solids were dissolved in ether
  8. dry with materialthe solution was dried with magnesium sulfate
  9. filtrationfiltered
  10. customevaporated on a rotary evaporator
  11. customThe resulting solids were dried under vacuum
  12. customto give 59.66 g (84% yield)
  13. customrecrystallized from hot toluene (100 mL)
  14. additionby adding cyclohexane (250 mL)
  15. customThe crystals were collected
  16. washwashed with cyclohexane
  17. customdried under vacuum

Sources & evidence

ORD record
ord-f6cc7c3b90634e87be52c1855ce21dee
Source dataset
uspto-grants-2011_01
Patent number
US07868086B2

Reaction notes

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