4-But-2-ynyloxy-benzenesulfonyl chloride → 4-But-2-ynyloxybenzenesulfonyl fluoride

HRID 353562Notes

Reaction equation

HRID 353562 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[F-:16].[K+].[F-].[F-].[Ca+2]>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([F:16])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

3

Reactant 2

HCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 23699612Calcium;potassium;trifluoride

Product 1

HCID 111955204-But-2-ynyloxybenzenesulfonyl fluorideYield 80.3%

Procedure

To a solution of 4-but-2-ynyloxybenzenesulfonyl chloride (prepared from Example 30, step 4) (2.0 g, 8.18 mmol) in acetonitrle (10 ml) was added KF-CaF2 (2.85 g, 16.3 mmol) and the resulting mixture was stirred for 4 hours at room temperature. The reaction mixture was filtered and the filterate was concentrated. The crude product was dissolved in EtOAc and washed with water. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed to obtain 1.5 g (80%) of the product as solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filterate was concentrated
  3. dissolutionThe crude product was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-aa4edae5bb024e578df609a95718aa8d
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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