Hydrochloric Acid → HCID 22467807, compound

HRID 1387724Notes

Reaction equation

HRID 1387724 reaction equation
[Br:1][C:2]([F:22])([F:21])[C:3]([F:20])([F:19])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[Br:14])[CH:6]=1.[Cl:23][S:24](O)(=[O:26])=[O:25].Cl>C(Cl)(Cl)Cl>[Br:1][C:2]([F:21])([F:22])[C:3]([F:19])([F:20])[O:4][C:5]1[CH:6]=[C:7]([O:11][C:12]([F:17])([F:18])[C:13]([F:15])([F:16])[Br:14])[CH:8]=[CH:9][C:10]=1[S:24]([Cl:23])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24638Chlorosulfonic acidHCID 15880045HCID 15880045, compound

Product 1

HCID 22467807HCID 22467807, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a 250 mL of round-bottom flask resting in an ice-bath were placed 23.35 g (0.05 mol) of this 1,3-di(2-bromotetrafluoroethoxy)benzene and 100 mL of chloroform. Then 116 g of chlorosulfonic acid was added dropwise into the solution. After the initial evolution of hydrogen chloride had subsided, the mixture was brought to room temperature. The reaction mixture was stirred at room temperature for 1 hour, then heated at 35° C. for another day. The contents of the flask were poured into a 1 L beaker filled with crushed ice. The chloroform layer was separated and washed with ice cold water to neutral. The organic layer was dried over sodium sulfate. After the removal of the solid materials by filtration, the chloroform was evaporated off completely. The crude product was purified by distillation under the reduced pressure to collect the fraction boiling at 127-129° C./10−2 torr. A total of 25.1 g (0.0443 mol) of 2,4-bis(2-bromotetrafluoroethoxy)benzenesulfonyl chloride was obtained in 88.7% yield. The quantity of hydrogen by-product was below 3%.

Workup

  1. customIn a 250 mL of round-bottom flask resting in an ice-bath
  2. customwas brought to room temperature
  3. temperatureheated at 35° C. for another day
  4. additionThe contents of the flask were poured into a 1 L beaker
  5. additionfilled with crushed ice
  6. customThe chloroform layer was separated
  7. washwashed with ice cold water to neutral
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customAfter the removal of the solid materials
  10. filtrationby filtration
  11. customthe chloroform was evaporated off completely
  12. distillationThe crude product was purified by distillation under the reduced pressure
  13. customto collect the fraction boiling at 127-129° C./10−2 torr

Sources & evidence

ORD record
ord-e4e7f3a8106a442e9ccf52ff2e39bfdc
Source dataset
uspto-grants-2001_07
Patent number
US06268532B1

Reaction notes

Loading…