Réaction #2236

Équation de réaction

chlorosulphonic acid

2-(methanesulphonyloxy)methoxybenzene

oxalyl chloride

toluene

Oxalyl chloride

→

title compound

3-Methanesulphonyloxy-4-methoxybenzenesulphonyl chloride

Solvants

dichloromethane

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températuremaintaining the temperature below 0° C
2. 2
   Autreto rise to 10° C
3. 3
   AutreThe mixture was evaporated to dryness in vacuo
4. 4
   Autreto 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
   AutreThe solvent was evaporated in vacuo
9. 9
   Autrethe residue was purified by column chromatography on silica
10. 10
    Lavageeluting with 60% ethyl acetate in hexane

Mode opératoire

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.

Source