Water → ethyl 5-bromo-1H-pyrrole-2-carboxylate

Temperature

0 °C

Commercially available ethyl 1H-pyrrole-2-carboxylate (5.10 g, 30.7 mmol) was dissolved in a mixed solvent of tetrahydrofuran (120 mL) and methanol (60 mL), and cooled to 0° C. N-Bromosuccinimide (6.52 g, 30.7 mmol) was added, and stirring was carried out at room temperature for 18 hours under nitrogen atmosphere. Water (150 mL) and ethyl acetate (200 mL) were added, and the solution was separated. 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=5%-30%) to afford the desired compound (3.20 g, yield 40%) as a white solid.

1. customthe solution was separated
2. washThe organic layer was washed with saturated brine
3. dry with materialsubsequently dried over anhydrous magnesium sulfate
4. distillationThe solvent was distilled off under reduced pressure
5. customthe resulting residue was purified
6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=5%-30%)

ORD record

ord-c63e9babc02c406fabcc41735a0cded2

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415359B2