4-Methoxybenzenesulfonyl chloride → 4-Methoxybenzene-1-sulfonyl fluoride

HRID 1475329Notes

Reaction equation

HRID 1475329 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[F-:13].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([F:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 124097114-Methoxybenzene-1-sulfonyl fluorideYield 85.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-methoxy-benzenesulfonyl chloride (1.0 g, 4.8 mmol) in acetonitrile (20 mL) was added KF (563 mg, 9.7 mmol) and the resulting mixture was stirred for 16 h at room temperature. The solid was filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and washed with water. The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (780 mg) as a colourless oil. 1H NMR (CDCl3): 7.97 (2H, d), 7.09 (2H, d), 3.94 (3H, s).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f5dca5a501447548a17200bdcc069dd
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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