Phosphorus oxychloride → HCID 18739166, compound

HRID 1387722Notes

Reaction equation

HRID 1387722 reaction equation
[Br:1][C:2]([F:26])([F:25])[C:3]([F:24])([F:23])[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[Br:14])=[CH:7][C:6]=1[S:19](O)(=[O:21])=[O:20].[K].S1(CCCC1)(=O)=O.P(Cl)(Cl)([Cl:37])=O>C(Cl)Cl.C(#N)C>[Br:1][C:2]([F:26])([F:25])[C:3]([F:24])([F:23])[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[Br:14])=[CH:7][C:6]=1[S:19]([Cl:37])(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 31347SulfolaneHCID 5462222PotassiumHCID 18739169HCID 18739169, compound

Product 1

HCID 18739166HCID 18739166, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5.86 g (0.01 mol) of the 2,5-di(2-bromotetrafluoroethoxy) benzenesulfonic acid, potassium salt, 10 mL acetonitrile, 10 mL sulfolane and 6 mL phosphoryl chloride was placed into a 100 mL round-bottom flask, and stirred at 68-82° C. for 1 hour. The mixture was then cooled down to below 5° C. (with the reaction vessel resting in an ice-bath) and 15 mL ice-cold water was added dropwise. Stirring was continued at a temperature below 10° C. for 20 minutes and the precipitated oily product was isolated by suction and then diluted with 100 mL of methylene chloride. The combined organic layer was washed with saturated aq. sodium chloride in a 500 mL separatory funnel until neutral and dried over sodium sulfate overnight. After the removal of the salt by filtration and the evaporation of the solvents, the crude product was purified by distillation at reduced pressure (10 to 10−2 torr) to collect 102-106° C. fraction at vacuum. A total of 5.00 g (0.0088 mol) of 2,5-di(2-bromotetrafluoroethoxy) benzenesulfonyl chloride was obtained in 88.2% yield.

Workup

  1. customwas placed into a 100 mL round-bottom flask
  2. temperatureThe mixture was then cooled down to below 5° C. (with the reaction vessel
  3. customresting in an ice-bath
  4. stirringStirring
  5. waitwas continued at a temperature below 10° C. for 20 minutes
  6. customthe precipitated oily product was isolated by suction
  7. washThe combined organic layer was washed with saturated aq. sodium chloride in a 500 mL separatory funnel until neutral and
  8. dry with materialdried over sodium sulfate overnight
  9. customAfter the removal of the salt
  10. filtrationby filtration
  11. customthe evaporation of the solvents
  12. distillationthe crude product was purified by distillation at reduced pressure (10 to 10−2 torr)
  13. customto collect 102-106° C. fraction at vacuum

Sources & evidence

ORD record
ord-cccbf1ad463041c692350a25c6173d88
Source dataset
uspto-grants-2001_07
Patent number
US06268532B1

Reaction notes

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