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

HRID 278344Notes

Reaction equation

HRID 278344 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-62efb4c525574cd2adbb7c5d4b559db0
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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