1,3-Dibromopropane → 1-(4-(Benzyloxy)-3-methoxyphenyl)-cyclobutanecarbonitrile

Participants

Reaction Steps

To a solution of 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile (3.1 g, 12.24 mmol) in dichloromethane (30 mL) was added sodium hydroxide (30 mL, 50% aqueous solution, 367 mmol), TBAB (0.99 g, 3.06 mmol) and then with 1,3-dibromopropane (2 mL, 19.58 mmol). The reaction was stirred at room temperature for 72 hours. The layers were separated, organic layer was dried (MgSO4) and concentrated. Purification by flash chromatography (silica gel, 5-25% EtOAc/hexane) afforded 1-(4-(benzyloxy)-3-methoxyphenyl)cyclobutanecarbonitrile (1.8 g, 50%). MS (ESI) m/z 294 (M+H)+.

Provenance & Evidence