4-(4-Fluorophenoxy)benzenesulphonyl chloride → 4-(4-Fluorophenoxy)benzene-1-thiol

HRID 1872882Notes

Reaction equation

HRID 1872882 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19](Cl)(=O)=O)=[CH:15][CH:14]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 217055854-(4-Fluorophenoxy)benzene-1-thiolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (9.95 grams, 0.26 mole) was added in portions to a stirred solution of 4-(4-fluorophenoxy)benzenesulfonylchloride (30 grams, 0.105 mole) in tetrahydrofuran (700 mL). The resulting mixture was heated at reflux for 1.5 hours, cooled in an ice bath and quenched by addition of 10% aqueous sulfuric acid solution (100 mL). After stirring for 30 minutes, the mixture was filtered through Celite™ and the tetrahydrofuran was removed under vacuum. The residue was diluted with water and extracted with diethyl ether. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated under vacuum to provide the title compound as a white solid (23 grams, 100%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. temperaturecooled in an ice bath
  4. customquenched by addition of 10% aqueous sulfuric acid solution (100 mL)
  5. filtrationthe mixture was filtered through Celite™
  6. customthe tetrahydrofuran was removed under vacuum
  7. additionThe residue was diluted with water
  8. extractionextracted with diethyl ether
  9. washThe organic layer was washed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-349d59eb47f4417e8157bb11153bff4a
Source dataset
uspto-grants-2000_08
Patent number
US06110964

Reaction notes

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