(Prop-2-ynylsulfinyl)benzene → 3-(Chloromethyl)benzo(b)thiophene

Participants

Reaction Conditions

Reaction Steps

In 50 mL of 1,4-dioxane, was dissolved 5.02 g (30.6 mmol) of the compound obtained in Example 12. The resulting solution was heated at 100° C. After 5 hours and 30 minutes, the solution was cooled to keep the internal temperature of the reaction system at 10° C. To the cooled solution, was subsequently added 8.42 mL (33.7 mmol) of a 4 M hydrogen chloride-dioxane solution. The obtained mixture was allowed to stand at room temperature. After 15 minutes, the reaction liquid was concentrated and dissolved in 50 mL of ethyl acetate. The resulting solution was washed with 40 mL of water. The organic layer was dried with magnesium sulfate. After concentrating, the concentrate was redissolved in 50 mL of ethyl acetate in order to remove the dioxane. The obtained solution was washed with 40 mL of water three times. The organic layer was dried over magnesium sulfate and vacuum concentrated to provide 5.18 g of 3-(chloromethyl)-benzo[b]thiophene. The yield was 93%.

Provenance & Evidence