반응 #475644

반응 방정식

AlCl3

3,5-dimethylbenzenethiol

oxalyl chloride

→

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

수율 36.1%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도is heated to 120° C. in a microwave reactor for 15 minutes
2. 2
   온도The solution is cooled
3. 3
   workup.ADDITIONis poured
4. 4
   기타into crushed ice
5. 5
   추출The solution is extracted with CH2Cl2
6. 6
   기타the organic layer is collected
7. 7
   건조The solution is dried with MgSO4
8. 8
   여과is filtered
9. 9
   농축The filtrate is concentrated
10. 10
    기타the residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent

실험 절차

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%).

출처