Triethylamine → N-(2-Methoxybenzoyl)-2-bromopyrrole

Participants

Reaction Steps

To the stirred solution of 2-bromo-pyrrole (22.3 mmol) in 60 mL of dry THF and 120 mL of CH2Cl2 at -78° C. in an atmosphere of nitrogen, was added triethylamine (6.22 mL, 44.6 mmol) followed immediately by dropwise addition of a solution of 2-methoxybenzoyl chloride (5.0 mL, 33.6 mmol) in 40 mL CH2Cl2. The reaction mixture was stirred overnight while it was allowed to warm to room temperature. The mixture was washed with water and brine, dried (Na2SO4) and concentrated in vacuo at room temperature. The crude product was purified by chromatography on triethylamine-treated neutral silica, using EtOAc-Hex (5:95) as the eluent, to give 3.81 g of the title compound as a colorless oil. 1H NMR (CDCl3) δ: 7.58-7.36 (2 H, m), 7.10-6.86 (3 H, m), 6.36 (1 H, dd, J=3.5, 1.8), 6.16 (1 H, t, J=3.5), 3.78 (3 H, s).

Provenance & Evidence