4-Fluorobiphenyl → 4-Fluorobiphenylsulfonyl Chloride

HRID 1531231Notes

Reaction equation

HRID 1531231 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-30307af61b604ce9be93b965f12d99d0
Source dataset
uspto-grants-2001_03
Patent number
US06197810B1

Reaction notes

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