Reaction #66017

Reaction equation

sulphonic acid

4-phenoxybenzenesulphonic acid

thionyl chloride

→

4-Phenoxy-benzenesulphonyl chloride

Solvents

DMF

Conditions

Workup

1. 1
   Temperatureat reflux
2. 2
   OtherThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue dissolved in Et20 (40 mL)
4. 4
   WashThe ether solution was washed with 5% aqueous NaOH (3×40 mL) and water (6×40 mL)
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   OtherAfter drying in high vacuum overnight
9. 9
   Otherthe pure product was obtained as a white solid

Procedure

The sulphonic acid (2a) was dissolved in an excess of thionyl chloride (30 mL), a catalytic amount of DMF (cat) was added, and the resulting mixture was stirred for 6 h at reflux. The solvent was evaporated and the residue dissolved in Et20 (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 63%: 2.09 g, 7.44 mmol, (light yellow syrup). 1H-NMR (CDCl3): δ 7.44 (d, 3J=9.1 Hz, 2H, ArH), 7.38 (d, 3J=9.1 Hz, 2H, ArH), 7.19 (t, 1H, ArH), 7.12 (d, 3J=9.1 Hz, 2H, ArH), 6.98 (d, 3J=9.1 Hz, 2H, ArH)

Source