Water → (4-Fluoro-3-phenoxyphenyl)methanesulfonyl fluoride

HRID 479887Notes

Reaction equation

HRID 479887 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9](Cl)(=[O:11])=[O:10])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F-:20].[K+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([F:20])(=[O:11])=[O:10])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 2724141Tetrabutylammonium FluorideHCID 18000351(4-Fluoro-3-phenoxyphenyl)methanesulfonyl chloride

Product 1

HCID 12113197(4-Fluoro-3-phenoxyphenyl)methanesulfonyl fluorideYield 42.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The sulfonyl chloride obtained in step 2 (2.0 g, 6.65 mmol) is diluted with acetonitrile (20 ml). The resultant solution is treated with potassium fluoride (1.93 g, 33.25 mmol) and tetrabutylamonium fluoride (0.208 g, 0.66 mmol), stirred at room temperature for one day, poured into water, and extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash chromatography of the residue on silica gel eluting with 15:85 ethyl acetate/hexanes gives (4-fluoro-3-phenoxyphenyl)methanesulfonyl fluoride (0.81 g, mp 59.5-61.5° C.) which is identified by 1H and 19F NMR spectral analyses.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washis washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-368e7d1eecd54a55aa9215cc14301383
Source dataset
uspto-grants-2003_11
Patent number
US06646166B1

Reaction notes

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