Reaktion #2236

Reaktionsgleichung

chlorosulphonic acid

2-(methanesulphonyloxy)methoxybenzene

oxalyl chloride

toluene

Oxalyl chloride

→

title compound

3-Methanesulphonyloxy-4-methoxybenzenesulphonyl chloride

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintaining the temperature below 0° C
2. 2
   Sonstigeto rise to 10° C
3. 3
   SonstigeThe mixture was evaporated to dryness in vacuo
4. 4
   Sonstigeto yield an oil which
5. 5
   workup.STIRRINGwith stirring under a nitrogen atmosphere
6. 6
   workup.STIRRINGAfter stirring for 2 hours at room temperature
7. 7
   workup.STIRRINGthe reaction stirred overnight
8. 8
   SonstigeThe solvent was evaporated in vacuo
9. 9
   Sonstigethe residue was purified by column chromatography on silica
10. 10
    Wascheneluting with 60% ethyl acetate in hexane

Vorschrift

A solution of 2-(methanesulphonyloxy)methoxybenzene (0.822 g) in dichloromethane (15 ml) was stirred and cooled to -10° C. under a nitrogen atmosphere. A solution of chlorosulphonic acid (0.27 ml) in dichloromethane (5 ml) was then added dropwise over a period of 1 hour, maintaining the temperature below 0° C. The mixture was stirred for a further 4 hours, allowing the temperature to rise to 10° C. The mixture was evaporated to dryness in vacuo to yield an oil which was suspended in toluene (20 ml) with stirring under a nitrogen atmosphere. Oxalyl chloride (0.36 ml) was added dropwise, followed by the addition of DMF (5 drops). After stirring for 2 hours at room temperature, dichloromethane (15 ml) and oxalyl chloride (0.36 ml) were added and the reaction stirred overnight. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica, eluting with 60% ethyl acetate in hexane to furnish the title compound (0.99 g) as a white crystalline solid.

Quelle