Hexafluoropropylene → 1,1,2,3,3,3-Hexafluoro-2-iodopropyl sulfurofluoridate

HRID 1276569

Reaction equation

HRID 1276569 reaction equation
[I:1]Cl.[F:3][S:4]([OH:7])(=[O:6])=[O:5].[F:8][C:9]([F:16])([F:15])[C:10]([F:14])=[C:11]([F:13])[F:12]>>[S:4]([F:3])([O:7][C:11]([F:13])([F:12])[C:10]([F:14])([I:1])[C:9]([F:16])([F:15])[F:8])(=[O:6])=[O:5]

Participants

4

Reactant 3

HCID 8302HexafluoropropyleneHCID 24603Fluorosulfuric acidHCID 24640Iodine chloride

Product 1

HCID 125963661,1,2,3,3,3-Hexafluoro-2-iodopropyl sulfurofluoridateYield 40%

Procedure

Into a 1.3-liter stainless steel tube was charged a mixture of iodine monochloride (130 g, 0.80 mol) and fluorosulfonic acid (88 g, 0.88 mol). The tube was sealed and cooled, then hexafluoropropylene (144 g, 0.96 mol) was transferred into the tube. The reaction mixture was kept at 25° C. for 2 hr, 50° C. for 2 hr and 80° C. for 4 hr. The product was unloaded from the shaker tube and poured into ice water. The bottom organic layer was separated, washed with water and distilled to afford the title product (120 g, 40% yield) as a clear liquid, bp. 47° C./6.7 kPa. 19F NMR (188.24 MHz, CDCl3): -74.5 (m, 3F), -77.0 (m, AB-pattern, 2F), -148.2 (m, 1F), +49.7 (m, 1F).

Workup

  1. additionInto a 1.3-liter stainless steel tube was charged
  2. customThe tube was sealed
  3. temperaturecooled
  4. customThe bottom organic layer was separated
  5. washwashed with water
  6. distillationdistilled

Sources & evidence

ORD record
ord-13d3a2bcbb4b4bf4900d4d47989ac5e8
Source dataset
uspto-grants-2000_12
Patent number
US06166157

Linked notes

Loading…