Réaction #475644

Équation de réaction

AlCl3

3,5-dimethylbenzenethiol

oxalyl chloride

→

4,6-dimethyl-benzo[b]thiophene-2,3-dione

Rendement 36.1%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Températureis heated to 120° C. in a microwave reactor for 15 minutes
2. 2
   TempératureThe solution is cooled
3. 3
   workup.ADDITIONis poured
4. 4
   Autreinto crushed ice
5. 5
   ExtractionThe solution is extracted with CH2Cl2
6. 6
   Autrethe organic layer is collected
7. 7
   SéchageThe solution is dried with MgSO4
8. 8
   Filtrationis filtered
9. 9
   ConcentrationThe filtrate is concentrated
10. 10
    Autrethe residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent

Mode opératoire

To a solution of AlCl3(0.4 g, 3.6 mmol) in CH2Cl2 (4 mL) at −20° C. under nitrogen are added 3,5-dimethylbenzenethiol (1 g, 7.2 mmol) and oxalyl chloride (0.6 mL, 7.2 mmol) respectively. The solution is warmed to room temperature for 1 hour and is heated to 120° C. in a microwave reactor for 15 minutes. The solution is cooled and is poured into crushed ice. The solution is extracted with CH2Cl2 and the organic layer is collected. The solution is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent to afford 4,6-dimethyl-benzo[b]thiophene-2,3-dione (500 mg, 35%).

Source