Hydrochloric Acid → HCID 22467807, compound

HRID 1934782Notes

Reaction equation

HRID 1934782 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 1L 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. additionfilled with crushed ice
  5. customThe chloroform layer was separated
  6. washwashed with ice cold water to neutral
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customAfter the removal of the solid materials
  9. filtrationby filtration
  10. customthe chloroform was evaporated off completely
  11. distillationThe crude product was purified by distillation under the reduced pressure
  12. customto collect the fraction boiling at 127-129° C./10−2 torr

Sources & evidence

ORD record
ord-a8f2dabb0eb14e438afd9db991492b11
Source dataset
uspto-grants-2002_05
Patent number
US06384167B2

Reaction notes

Loading…