Hydrochloric Acid → Benzene, 1,1'-sulfonylbis(4-fluoro-

HRID 637811Notes

Reaction equation

HRID 637811 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=O)=[CH:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ClS(O)(=O)=O.Cl>O>[CH:14]1[C:13]([F:12])=[CH:18][CH:17]=[C:16]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)(=[O:10])=[O:11])[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10008Fluorobenzene2×HCID 24638Chlorosulfonic acidHCID 468864-Fluorobenzenesulfonic acid

Product 1

HCID 67842Benzene, 1,1'-sulfonylbis(4-fluoro-Yield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 194 g (1.1 moles) quantity of 4-fluorobenzenesulfonic acid was added to 96 g (1 mole) of fluorobenzene and the mixture was cooled with water while 123 g (1.1 moles) of chlorosulfonic acid was added at about 10° to about 20° C. over a period of 1 hour. After the addition, the reaction mixture was stirred for 3 hours while being maintained at 20° to 30° C. The hydrochloric acid gas evolved during the reaction was continuously removed from the reaction system. After the completion of the reaction, about 400 ml of water was added to the reaction mixture, and 9.6 g (0.1 mole) of the unreacted fluorobenzene was recovered by distillation. Separation of the precipitate by filtration gave 65 g of 4,4'-difluorodiphenylsulfone in 58% yield. M.P. 97° to 98° C. Purity of 99.7%.

Workup

  1. additionwas added at about 10° to about 20° C. over a period of 1 hour
  2. additionAfter the addition
  3. temperaturewhile being maintained at 20° to 30° C
  4. customwas continuously removed from the reaction system
  5. customAfter the completion of the reaction, about 400 ml of water
  6. distillationwas recovered by distillation
  7. customSeparation of the precipitate
  8. filtrationby filtration

Sources & evidence

ORD record
ord-4a8a85cb45f649fca68efe768070b3ba
Source dataset
uspto-grants-1985_12
Patent number
US04558161

Reaction notes

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