Ethyl Bromide → 1-(4-Ethoxy-2-methylphenyl)-2,5-dimethyl-1H-pyrrole

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-hydroxy-2-methylphenyl)-2,5-dimethylpyrrole (˜50 mmol) in acetonitrile (300 mL) was added potassium carbonate (55 mmol) and an excess of bromoethane (>100 mmol). The reaction mixture was stirred at 50° C. overnight, cooled to room temperature, and partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (15% EtOAc/hexanes) to give 2,5-dimethyl-1-(4-ethoxy-2-methylphenyl)pyrrole as a colorless oil: 1H NMR (CDCl3, 500 MHz) δ 7.07 (d, 1H), 6.84 (d, 1H), 6.79 (dd, 1H), 5.90 (s, 2H), 4.07 (q, 2H), 1.92 (s, 6H), 1.90 (s, 3H), 1.45 (t, 3H; MS (ESI) 230 (M+H)+.

Provenance & Evidence