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

Participants

Reaction Steps

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%).

Provenance & Evidence