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

Temperature

100 °C

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%.

1. temperature30 minutes, the solution was cooled
2. customat 10° C
3. customto stand at room temperature
4. waitAfter 15 minutes
5. customthe reaction liquid
6. concentrationwas concentrated
7. dissolutiondissolved in 50 mL of ethyl acetate
8. washThe resulting solution was washed with 40 mL of water
9. dry with materialThe organic layer was dried with magnesium sulfate
10. concentrationAfter concentrating
11. dissolutionthe concentrate was redissolved in 50 mL of ethyl acetate in order
12. customto remove the dioxane
13. washThe obtained solution was washed with 40 mL of water three times
14. dry with materialThe organic layer was dried over magnesium sulfate and vacuum
15. concentrationconcentrated

ORD record

ord-fc275280caa141bf90f87297a20a67b6

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884896B2