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

HRID 2175176Notes

Reaction equation

HRID 2175176 reaction equation
[Cl-].[Al+3].[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of aluminum chloride (AlCl3) (0.4 g, 3.6 mmol) in CH2Cl2 (4 mL) at −20° C. under nitrogen were added 3,5-dimethylbenzenethiol (1 g, 7.2 mmol) and oxalyl chloride (0.6 mL, 7.2 mmol) respectively. The solution was warmed to room temperature for 1 hour and was heated to 120° C. in a microwave reactor for 15 minutes. The solution was cooled down and was poured into crashed ice. The solution was extracted with CH2Cl2 and the organic layer was collected. The solution was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by silica gel flash column chromatography with 5% EtOAc in Hexane as the eluent to afford the title compound (500 mg, 35%).

Workup

  1. temperaturewas heated to 120° C. in a microwave reactor for 15 minutes
  2. temperatureThe solution was cooled down
  3. additionwas poured
  4. extractionThe solution was extracted with CH2Cl2
  5. customthe organic layer was collected
  6. dry with materialThe solution was dried with MgSO4
  7. filtrationwas filtered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was purified by silica gel flash column chromatography with 5% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-f59fabf77bb64b3dbddc73b3261c7f5b
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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