Thionyl Chloride → HCID 17952798, compound

Temperature

50 °C

(4-Acetyl-phenylsulfanyl)-acetic acid (1.0 g, 4.8 mmol) is suspended in dichloroethane, under nitrogen at ambient temperature. To this is added thionyl chloride (0.694 ml, 9.6 mmol) followed immediately by 1 drop of DMF. After maintaining the reaction mixture at 50° C. for 30 min., the mixture became homogenous. After cooling to ambient temperature, nitrogen was bubbled into the mixture to remove any trace gasses (10 min.), then aluminum trichloride (1.9 g, 14.4 mmol) was added in 4 portions which caused the reaction temperature to raise to 40° C. After the reaction had cooled to ambient temperature (2 hr), the reaction mixture was poured into 200 mL of and ice/water mixture and extracted with dichloromethane (3×100 ml). The combined organic layers were washed with saturated bicarbonate solution, and brine, then dried over MgSO4, filtered and concentrated in vacuo to yield 5-acetyl-benzo[b]thiophen-3-one as a red brown solid (720 mg, 79%). This material was used without further purification. 1H NMR (250 MHz, CDCl3): δ 8.23 (d, 1H, J=2.1), 8.15 (dd, 1H, J=7.5,J=2.1), 7.48 (d, 1H, J=7.5), 3.83 (s, 2H), 2.56 (s, 3H). MS [EI+] 193 (M+H)+, [EI−] 191 (M−H)−.

1. temperatureAfter cooling to ambient temperature
2. customnitrogen was bubbled into the mixture
3. customto remove any trace gasses (10 min.)
4. temperatureto raise to 40° C
5. temperatureAfter the reaction had cooled to ambient temperature (2 hr)
6. extractionextracted with dichloromethane (3×100 ml)
7. washThe combined organic layers were washed with saturated bicarbonate solution, and brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-5dc49b8f77124deea2276b1de9937935

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348359B2