4-Fluorobiphenyl → 4'-Fluorobiphenylsulfonyl Chloride

HRID 1359042Notes

Reaction equation

HRID 1359042 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:8]=[CH:9][C:10]([C:13]2[C:14]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 94614-FluorobiphenylHCID 24638Chlorosulfonic acid

Product 1

HCID 181794554'-Fluorobiphenylsulfonyl Chloride

Procedure

Chlorosulfonic acid (8.7 mL, 0.13 mole) was added dropwise to stirred cold (0° C.) 4-fluorobiphenyl (10.2 g, 59 mmol). After 30 minutes at 0° C. 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, brine, dried over magnesium sulfate, and concentrated to afford a white solid. The desired 4′-fluorobiphenylsulfonyl chloride (4.3 g), was separated from 4′-fluorobiphenylsulfonic acid by crystallization of the latter from ethyl acetate and crystallization of the remaining material from hexanes.

Workup

  1. additionAfter 30 minutes at 0° C. the reaction mixture was poured onto ice
  2. filtrationThe resulting white precipitate was collected by filtration
  3. dissolutiondissolved in chloroform
  4. washThe chloroform solution was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto afford a white solid
  8. customThe desired 4′-fluorobiphenylsulfonyl chloride (4.3 g), was separated from 4′-fluorobiphenylsulfonic acid by crystallization of the latter from ethyl acetate and crystallization of the remaining material from hexanes

Sources & evidence

ORD record
ord-570a4d5597fc4d7e9a45e462175d2bf5
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

Loading…