3-Nitrobenzenesulfonyl chloride → Benzenesulfonyl fluoride, 3-nitro-

HRID 341755Notes

Reaction equation

HRID 341755 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F-:14].[K+]>O1CCOCC1.O>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([F:14])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 67683Benzenesulfonyl fluoride, 3-nitro-Yield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Nitrobenzenesulphonyl chloride (10 g) was dissolved in 1,4-dioxane (30 ml) and stirred at room temperature. To this solution was added a solution of potassium fluoride (3.9 g) in water (5 ml) and the stirring continued at room temperature for 5 hours. The reaction mixture was allowed to stand at room temperature overnight and was poured into ice/water. The product was extracted into dichloromethane, the solvent was dried (MgSO4) and evaporated under reduced pressure to give the title compound (8 g). This material was sufficiently pure for the next stage of the synthesis.

Workup

  1. waitto stand at room temperature overnight
  2. extractionThe product was extracted into dichloromethane
  3. dry with materialthe solvent was dried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b6aef9a995ae42ac81fe40f748cce905
Source dataset
uspto-grants-1999_01
Patent number
US05856273

Reaction notes

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