Potassium Carbonate → 3-Bromo-4-cyclobutoxybenzonitrile

Participants

Reaction Steps

Bromocyclobutane (2.7 g, 20.2 mmol), 3-bromo-4-hydroxybenzonitrile (2.0 g, 10.1 mmol), and K2CO3 (2.8 g, 20.2 mmol) were mixed in 5 mL of dimethylformamide and reacted at 60° C. for 72 hours. The mixture was diluted with ethyl acetate, washed with water, brine, dried with MgSO4, filtered, and the solvent removed under reduced pressure. The residue was chromatographed (SiO2) using a gradient from hexane to 30% ethyl acetate in hexane over 500 mL to afford the title compound. (2.2 g, 8.7 mmol, 86% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.69-1.82 (m, 1H), 1.87-2.00 (m, 1H), 2.21-2.35 (m, 2H), 2.45-2.57 (m, 2H), 4.69-4.79 (m, 1H), 6.76 (d, J=8.48 Hz, 1H), 7.53 (dd, J=8.48, 2.03 Hz, 1H), 7.82 (d, J=2.03 Hz, 1H). MS (DCI/NH3) m/z 251.9 (M+H)+.

Provenance & Evidence