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

Participants

Reaction Steps

NBS (6.4 g) was added in one portion to a stirred solution of 1-(triisopropylsilyl)pyrrole (8.00 g) in dry THF (80 mL) at -78° C. The mixture was stirred at this temperature for 2 h, and was then allowed to warm to room temperature overnight. The solvent was removed, water was added to the residue, and the product extracted with CH2Cl2, dried (anhyd Na2SO4), filtered, and evaporated. The residue was chromatographed over silica gel (hexanes) and concentrated to provide 10.00 g of 3-bromo-1-(triisopropylsilyl)pyrrole as a colorless oil.

Provenance & Evidence