Hydrochloric Acid → Benzo(b)thiophene-2,3-dione

To a solution of benzenthiol (1 ml, 9.7 mmol) in Et2O (30 ml) at 0° C. oxalyl chloride (0.94 ml, 10.7 mmol) was added dropwise. The mixture was stirred at room temperature for 1.5 hour, then, the solvent was evaporated under reduced pressure. The crude was dissolved in CH2Cl2 (40 ml) and a solution of AlCl3 (4.75 g, 35 mmol) in CH2Cl2 (32 ml) was added dropwise at 0° C. The mixture was stirred for 16 hours at room temperature, then, ice and 1M HCl were added until a clear mixture was obtained. After 1 hour, the phases were separated and the aqueous layer was extracted with CH2Cl2 (3×30 ml). The collected organic phases were dried over Na2SO4, filtered and evaporated, affording 18 (1.2 g, 78%) as orange solid that was used without further purification.

1. customthe solvent was evaporated under reduced pressure
2. dissolutionThe crude was dissolved in CH2Cl2 (40 ml)
3. stirringThe mixture was stirred for 16 hours at room temperature
4. customwas obtained
5. waitAfter 1 hour
6. customthe phases were separated
7. extractionthe aqueous layer was extracted with CH2Cl2 (3×30 ml)
8. dry with materialThe collected organic phases were dried over Na2SO4
9. filtrationfiltered
10. customevaporated

ORD record

ord-5dd89baaeae94135a4053910e4ebf138

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648076B2