18-Crown-6 → 3-Chloro-4-fluorobenzenesulfonyl fluoride

HRID 60417

Reaction equation

HRID 60417 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[F-:13].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([F:13])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 205117143-Chloro-4-fluorobenzenesulfonyl fluoride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the commercially available 3-chloro-4-fluorobenzenesulfonyl chloride (7 g, 30 mmol) in CH3CN (40 mL) was added KF (7 g, 120 mmol) and 18-crown-6 (0.5 g), then the mixture was stirred at room temperature overnight. The mixture was quenched with aqueous water and extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give the crude product which was purified by column to give the reagent R-12a (4.2 g, 95.5%) as a pale yellow solid. ESI-MS (M+1): 213.2 calc. for C6H3CIF2O2S

Workup

  1. customThe mixture was quenched with aqueous water
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4d2f9af19e2e475e8307933b0643585b
Source dataset
uspto-grants-2016_09
Patent number
US09440989B2

Linked notes

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