Pyridine → 3-Bromo-1-(triisopropylsilyl)pyrrole

Participants

Reaction Steps

NBS (N-bromosuccinimide; 0.8 g, 4.5 mmol) was added to a stirred solution of N-(triisopropylsilyl)pyrrole (1.0 g, 4.5 mmol) in anhydrous THF (10 mL) at −78° C. The reaction mixture was kept at −78° C. for 1-2 h and then left to reach room temperature (ca. 1 h). Pyridine (0.1 mL) and hexane (10 mL) were added, the resulting suspension was filtered through a plug of neutral alumina, and the filtrate was evaporated in vacuum. Purification by column chromatography on silica gel (hexane/ethyl acetate=10:1) gave oil (1.22 g, 90.1% yield). 1H NMR (CDCl3) δ 6 1.08 (d, 18 H, Hz, Me), 1.42 (sept, 3 H, CH), 6.26 (dd, 1H, H-4), 6.66 (t, 1 H, H-5), 6.72 (dd, 1H, H-2). MS (M+H) m/z 302.

Provenance & Evidence