Thionyl Chloride → 4-(4-Fluorophenoxy)benzenesulphonyl chloride

HRID 37741Notes

Reaction equation

HRID 37741 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13](O)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>CN(C=O)C>[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([Cl:21])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 110225964-(4-fluorophenoxy)benzenesulfonic Acid

Product 1

HCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sulphonic acid intermediate (2b) was then dissolved in an excess of thionyl chloride, a catalytic amount of DMF (few drops) was added, and the resulting mixture was stirred for 6 h at reflux. The solvent was evaporated and the residue dissolved in Et2O (40 mL). The ether solution was washed with 5% aqueous NaOH (3×40 mL) and water (6×40 mL), dried over anhydrous MgSO4, filtered, and concentrated in vacuo. After drying in high vacuum overnight, the pure product was obtained as a white solid. Yield: 1.04 g, 3.63 mmol, 72% (white solid). 1H-NMR (CDCl3): δ 7.99 (d, 3J=9.1 Hz, 2H, ArH), 7.19-7.02 (m, 6H, ArH).

Workup

  1. temperatureat reflux
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in Et2O (40 mL)
  4. washThe ether solution was washed with 5% aqueous NaOH (3×40 mL) and water (6×40 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customAfter drying in high vacuum overnight
  9. customthe pure product was obtained as a white solid

Sources & evidence

ORD record
ord-6cfb59fd918846f68e255b17a99d8886
Source dataset
uspto-grants-2013_09
Patent number
US08524194B2

Reaction notes

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