Oxalyl chloride → 4,6-Dimethylbenzothiophene-2,3-dione

HRID 388462노트

반응식

HRID 388462 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1[CH:7]=[C:8]([SH:13])[CH:9]=[C:10]([CH3:12])[CH:11]=1.[C:14](Cl)(=[O:18])[C:15](Cl)=[O:16]>C(Cl)Cl>[CH3:12][C:10]1[C:9]2[C:15](=[O:16])[C:14](=[O:18])[S:13][C:8]=2[CH:7]=[C:6]([CH3:5])[CH:11]=1

참가 물질

5

반응물 3

HCID 65578Oxalyl chlorideHCID 1175483,5-DimethylbenzenethiolHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 584974374,6-Dimethylbenzothiophene-2,3-dione수율 36.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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%).

후처리

  1. temperatureis heated to 120° C. in a microwave reactor for 15 minutes
  2. temperatureThe solution is cooled
  3. additionis poured
  4. custominto crushed ice
  5. extractionThe solution is extracted with CH2Cl2
  6. customthe organic layer is collected
  7. dry with materialThe solution is dried with MgSO4
  8. filtrationis filtered
  9. concentrationThe filtrate is concentrated
  10. customthe residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent

출처 및 근거

ORD 기록
ord-60e5c30b5e09448abd3291c410b6c9dc
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377949B2

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