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

Participants

Reaction Conditions

Reaction Steps

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%.

Provenance & Evidence