Perfluoro-1-butanesulfonyl fluoride → HCID 86674269, compound

HRID 405198Notes

Reaction equation

HRID 405198 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[C:9]([C:17]([F:20])([F:19])[F:18])=[CH:10][C:11]([OH:16])=[C:12]([CH:15]=1)[CH:13]=[O:14].[F:21][C:22]([F:37])([S:33](F)(=[O:35])=[O:34])[C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26]>C1COCC1>[F:37][C:22]([F:21])([S:33]([O:16][C:11]1[CH:10]=[C:9]([C:17]([F:18])([F:19])[F:20])[C:8]([Cl:7])=[CH:15][C:12]=1[CH:13]=[O:14])(=[O:35])=[O:34])[C:23]([F:31])([F:32])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26]

Participants

5

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 23665647Potassium tert-butoxideHCID 86674268HCID 86674268, compound

Product 1

HCID 86674269HCID 86674269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.04 M THF solution of t-BuOK (4.9 mL, 5.1 mmol) was added to a 0° C., THF solution (4 mL) of 5-chloro-2-hydroxy-4-(trifluoromethyl)benzaldehyde (1.0 g, 4.6 mmol). After 4 min, neat 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1.7 mL, 9.3 mmol) was added and the ice bath was removed. After 1 h at room temperature, AcOH (1 mL) was added and the resulting mixture was concentrated. The resulting material was diluted with DCM and 1M aqueous HCl, the layers were separated, and the organic layer was washed with 1 M NaHCO3, dried (Na2SO4), and concentrated to yield the title compound that was used without further purification.

Workup

  1. customthe ice bath was removed
  2. waitAfter 1 h at room temperature
  3. additionAcOH (1 mL) was added
  4. concentrationthe resulting mixture was concentrated
  5. additionThe resulting material was diluted with DCM and 1M aqueous HCl
  6. customthe layers were separated
  7. washthe organic layer was washed with 1 M NaHCO3
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2201bf8f26e44e1790dc8ce1c220b374
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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