2-Acetylpyrrole → 1-(5-Bromo-1H-pyrrol-2-yl)ethan-1-one

2-Acetylpyrrole (2.00 g, 18.3 mmol) was dissolved in a mixed solvent of tetrahydrofuran (100 mL) and methanol (50 mL), and N-bromosuccinimide (3.26 g, 18.3 mmol) was added with stirring at room temperature under nitrogen atmosphere. After stirring for 1 hour, the solvent was distilled off under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution (200 mL) was added, and extraction was carried out with ethyl acetate (300 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-20%) to afford the desired compound (770 mg, yield 22%) as a white solid.

1. additionwas added
2. stirringAfter stirring for 1 hour
3. distillationthe solvent was distilled off under reduced pressure
4. additionA saturated aqueous sodium hydrogencarbonate solution (200 mL) was added
5. extractionextraction
6. washThe organic layer was washed with saturated brine
7. dry with materialsubsequently dried over anhydrous magnesium sulfate
8. distillationThe solvent was distilled off under reduced pressure
9. customthe resulting residue was purified
10. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-20%)

ORD record

ord-7b4b3b7c21cf4e95a8763bba1a93f089

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415359B2