Perfluoro-1-butanesulfonyl fluoride → HCID 86674258, compound

HRID 405183Notes

Reaction equation

HRID 405183 reaction equation
CC([O-])(C)C.[K+].[OH:7][C:8]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[F:17][C:18]([F:33])([S:29](F)(=[O:31])=[O:30])[C:19]([F:28])([F:27])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22]>C1COCC1>[F:33][C:18]([F:17])([S:29]([O:7][C:8]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11])(=[O:31])=[O:30])[C:19]([F:27])([F:28])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 5227773-MethylsalicylaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 86674258HCID 86674258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.04 M THF solution of t-BuOK (3.7 mL, 3.9 mmol) was added to a THF solution (0.5 mL) of 2-hydroxy-3-methylbenzaldehyde (500 mg, 3.7 mmol) and 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1.16 g, 3.9 mmol) and the reaction was stirred at room temperature. After 30 min the temperature was increased to 40° C. After 5 min the resulting mixture was partitioned with DCM and water, and the aqueous layer was extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated to yield a 4:1 w/w mixture of the title compound and starting material, which mixture was used in the next step without further purification.

Workup

  1. temperatureAfter 30 min the temperature was increased to 40° C
  2. customAfter 5 min the resulting mixture was partitioned with DCM and water
  3. extractionthe aqueous layer was extracted with DCM
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customto yield

Sources & evidence

ORD record
ord-eef145cda05b4eb4898a954a983df632
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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