4-Methyl-1-(prop-2-ynylsulfinyl)benzene → 3-(Chloromethyl)-5-methylbenzo[b]thiophene

Temperature

100 °C

In 15 mL of dioxane, was dissolved 873.4 mg (4.9 mmol) of the compound obtained in Example 11. The resulting solution was stirred with heating at 100° C. for 70 minutes. The reaction system was cooled to room temperature, and 1.5 mL (6 mmol) of a 4 M hydrogen chloride-dioxane was added. The resulting mixture was stirred at room temperature for 1 hour. The reaction system was vacuum concentrated, and was added 0.80 mL of cyclohexane. The obtained mixture was heated at 70° C. for 10 minutes and cooled to room temperature. The resulting precipitates were filtered to obtain 590.6 mg of 3-(chloromethyl)-5-methylbenzo[b]thiophene. The yield was 61%.

1. temperatureThe reaction system was cooled to room temperature
2. stirringThe resulting mixture was stirred at room temperature for 1 hour
3. concentrationconcentrated
4. additionwas added 0.80 mL of cyclohexane
5. temperatureThe obtained mixture was heated at 70° C. for 10 minutes
6. temperaturecooled to room temperature
7. customThe resulting precipitates
8. filtrationwere filtered

ORD record

ord-a0ef35c684b2479bafb8dcb8f6c7dfdb

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884896B2