N-bromobutanimide → 3-Bromo-1-(triisopropylsilyl)pyrrole

Participants

Reaction Conditions

Reaction Steps

To a -78° C. solution under nitrogen of 1-triisopropylsilylpyrrole (2.8 g, 12.6 mmol) in THF (30 ml) was added NBS (2.23 g, 12.6 mmol) via a solid addition funnel. The reaction mixture was stirred at -78° C. for 1 hour and then was warmed to ambient temperature over 1 hour. The reaction mixture was concentrated, carbon tetrachloride was added to precipitate the succinimide and the solid was filtered and washed with carbon tetrachloride. The filtrate was concentrated, and the crude product was purified by flash chromatography (hexanes) to afford 3-bromo-1-triisopropylsilylpyrrole (3.18 g) as a colorless oil.

Provenance & Evidence