Hydrochloric Acid → HCID 57615036, compound

Temperature

20 °C

To dichloromethane (750 mL) suspension of 250 g of (4-bromophenylthio)acetic acid were added 2.5 mL of N,N-dimethylformamide and 132 g of thionyl chloride, which was then refluxed for 1 hour. After cooling the reaction mixture to 20° C., thereto was dropwise added dichloromethane (1500 mL) suspension of 148 g of aluminum chloride at 5 to 15° C., which was then stirred at 15 to 25° C. for 1.5 hours. Next, this reaction mixture was added dropwise to a mixed solution of 1310 mL of water and 188 mL of hydrochloric acid under cooling. The organic layer was separated, thereto was added 1250 mL of water, and the pH was adjusted to 3.0 with 5% potassium carbonate aqueous solution. The organic layer was separated and cooled to 5° C. Thereto were added 15.3 g of sodium borohydride and 500 mL of methanol, which was then stirred at 10 to 20° C. for 2 hours. To the reaction solution was added 750 mL of water, followed by adjustment to pH7.0 using acetic acid and left unattended in room temperature overnight. To the reaction solution was added 200 mL of 5% potassium hydroxide aqueous solution, and the organic layer was separated. To the organic layer was 25.0 g of activated carbon, which was then stirred at room temperature. Insoluble matter was filtered off, and the solvent of filtrate was distilled off. To the resultant residue was added cyclohexane, the crystals precipitated were collected by filtration to provide 194 g of 5-bromo-2,3-dihydro-1-benzothiophen-3-ol as pale red solid form.

1. temperaturewas then refluxed for 1 hour
2. temperatureunder cooling
3. customThe organic layer was separated
4. additionwas added 1250 mL of water
5. customThe organic layer was separated
6. temperaturecooled to 5° C
7. additionThereto were added 15.3 g of sodium borohydride and 500 mL of methanol, which
8. stirringwas then stirred at 10 to 20° C. for 2 hours
9. additionTo the reaction solution was added 750 mL of water
10. waitleft
11. waitunattended in room temperature overnight
12. additionTo the reaction solution was added 200 mL of 5% potassium hydroxide aqueous solution
13. customthe organic layer was separated
14. stirringwas then stirred at room temperature
15. filtrationInsoluble matter was filtered off
16. distillationthe solvent of filtrate was distilled off
17. additionTo the resultant residue was added cyclohexane
18. customthe crystals precipitated
19. filtrationwere collected by filtration

ORD record

ord-c992141139f7453ea22fb2582da6a8f7

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273902B2