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

HRID 388462

Reaktionsgleichung

Reaktionsgleichung von HRID 388462
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 584974374,6-Dimethylbenzothiophene-2,3-dioneAusbeute 36,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-60e5c30b5e09448abd3291c410b6c9dc
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377949B2

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