Acetyl chloride → 1-(5-Bromo-4-chlorothiophen-2-yl)ethan-1-one

2-Bromo-3-chlorothiophene (10.7 g, 51.5 mmol) was dissolved in dichloromethane (73.5 ml). The flask was equipped with a desiccant filled drying tube and the solution was chilled in an ice bath. Acetyl chloride (6.06 g, 77 mmol) was added followed by addition of aluminum trichloride (8.24 g, 61.8 mmol) over about 2 minutes (reaction bubbled vigorously as aluminum trichloride was added). The reaction mixture was stirred overnight, allowing to warm to room temperature, and then added cautiously and with stirring to a 1-L beaker containing ˜200 mL sat sodium bicarbonate. The mixture was stirred for 30 minutes and diluted with dichloromethane (˜100 mL). The layers were separated and the organic layer was washed with aqueous saturated sodium bicarbonate, water, and brine. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to give a crude solid. This material was recrystallized from hot hexanes to give the title compound.

1. customThe flask was equipped with
2. additiona desiccant filled
3. customdrying tube
4. temperaturethe solution was chilled in an ice bath
5. customreaction
6. custombubbled vigorously as aluminum trichloride
7. additionwas added)
8. additionadded cautiously
9. stirringwith stirring to a 1-L beaker
10. additioncontaining ˜200 mL
11. stirringThe mixture was stirred for 30 minutes
12. additiondiluted with dichloromethane (˜100 mL)
13. customThe layers were separated
14. washthe organic layer was washed with aqueous saturated sodium bicarbonate, water, and brine
15. dry with materialThe combined organic layers were dried with sodium sulfate
16. filtrationfiltered
17. concentrationconcentrated
18. customto give a crude solid
19. customThis material was recrystallized from hot hexanes

ORD record

ord-4b42f604831a4edc966d3fa94a076d94

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193723B2