4-Fluorobiphenyl → 4-Fluorobiphenylsulfonyl Chloride

HRID 2288116Notes

Reaction equation

HRID 2288116 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1>>[F:6][C:7]1[CH:12]=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 94614-FluorobiphenylHCID 24638Chlorosulfonic acid

Product 1

HCID 183240214-Fluorobiphenylsulfonyl Chloride

Procedure

Chlorosulfonic acid (8.7 mL, 0.13 mole) was added dropwise to 4-fluorobiphenyl (10.2 grams, 59 mmol) while stirring in an ice bath. Stirring was continued with ice cooling for 0.5 hours and then the reaction mixture was poured onto ice. The resulting white precipitate was collected by filtration and dissolved in chloroform. The chloroform solution was washed with water and brine, dried over magnesium sulfate and concentrated to afford a white solid. The desired product, 4-fluorobiphenylsulfonyl chloride (4.3 grams, 27%), was separated from 4-fluorobiphenylsulfonic acid (an unwanted side product) by crystallization of the latter from ethyl acetate and crystallization of the remaining material from hexane.

Workup

  1. stirringStirring
  2. additionthe reaction mixture was poured onto ice
  3. filtrationThe resulting white precipitate was collected by filtration
  4. dissolutiondissolved in chloroform
  5. washThe chloroform solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto afford a white solid
  9. customThe desired product, 4-fluorobiphenylsulfonyl chloride (4.3 grams, 27%), was separated from 4-fluorobiphenylsulfonic acid (an unwanted side product)
  10. customby crystallization of the latter
  11. customfrom ethyl acetate and crystallization of the remaining material from hexane

Sources & evidence

ORD record
ord-fbb943a0c4084e5ebe46b04736802847
Source dataset
uspto-grants-2000_07
Patent number
US06087392

Reaction notes

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