Perfluoro-1-butanesulfonyl fluoride → HCID 86755183, compound

HRID 378203Notes

Reaction equation

HRID 378203 reaction equation
[F:1][C:2]([F:33])([F:32])[O:3][C:4]([F:31])([O:9][C:10]([F:30])([O:15][C:16]([F:29])([F:28])[CH2:17][O:18][C:19](CCCCC(O)C)=[CH2:20])[C:11]([F:14])([F:13])[F:12])[C:5]([F:8])([F:7])[F:6].[F:34]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.N12CCCN=[C:57]1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2>C1(C)C=CC=CC=1>[F:1][C:2]([F:33])([F:32])[O:3][C:4]([F:31])([O:9][C:10]([F:30])([O:15][C:16]([F:29])([F:28])[CH2:17][O:18][C:19]([CH2:52][CH2:53][CH2:54][CH2:55][CH:56]([F:34])[CH3:57])=[CH2:20])[C:11]([F:14])([F:13])[F:12])[C:5]([F:8])([F:7])[F:6]

Participants

5

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86755181HCID 86755181, compound

Product 1

HCID 86755183HCID 86755183, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-15 °C

Procedure

Under a nitrogen atmosphere, (R)-8-(2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-7-hydroxyoct-1-ene (60 g, 0.103 mol) and dry toluene (120 mL) were added to an oven-dried flask with stirring. The resulting solution was cooled to -15° C., perfluorobutanesulfonyl fluoride (58.9 g, 0.185 mol) was added, and the resulting reaction mixture was stirred for 5 minutes. 1,8-Diazabicyclo[5.4.0]undec-7-ene (28.7 g, 0.189 mol) was then added at a rate so as not to exceed a temperature of 5° C. for the reaction mixture. The reaction mixture was stirred for 1 hour at ambient temperature and was quenched by the addition of toluene (120 mL) and water (60 mL). The resulting organic phase was separated from the resulting aqueous phase, and the aqueous phase was washed with toluene. The combined organic extracts were washed with 120 mL of 7 volume % HCl. The combined extracts were concentrated under reduced pressure (25 torr), and the resulting crude product was distilled (b.p. 58-° C. at 0.01 torr) to give 33.8 g of (S)-8-(2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-7-fluorooct-1-ene.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred for 5 minutes
  3. customa temperature of 5° C.
  4. stirringThe reaction mixture was stirred for 1 hour at ambient temperature
  5. customwas quenched by the addition of toluene (120 mL) and water (60 mL)
  6. customThe resulting organic phase was separated from the resulting aqueous phase
  7. washthe aqueous phase was washed with toluene
  8. washThe combined organic extracts were washed with 120 mL of 7 volume % HCl
  9. concentrationThe combined extracts were concentrated under reduced pressure (25 torr)
  10. distillationthe resulting crude product was distilled (b.p. 58-° C. at 0.01 torr)

Sources & evidence

ORD record
ord-3de56d9390a645c6824755db5f4e1ad4
Source dataset
uspto-grants-2000_02
Patent number
US06030547

Reaction notes

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