Hydrochloric Acid → HCID 71743724, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-5-fluoro-benzonitrile (1 g, 5 mmol) and Ti(Oi-Pr)4 (1.81 mL, 5.5 mmol) in ether (20 mL) was added EtMgBr (3.67 mL, 11 mmol) at −78° C. After stirring at −78° C. for 10 min, the solution was warmed up to room temperature and stirred for 1 hour. BF3-Et2O (1.25 mL) was added before it was stirred for another 1 hour. After addition of 1 N aq. HCl (15 mL) and ether (30 mL), aq. NaOH (10%, 45 mL) solution was added to give two clear phases. The mixture was exacted with EtOAc (30 mL×5). The combined organic layers were dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product, which was purified by column chromatography (PE:EA=5:1) to afford the title compound (800 mg, 70%) as oil.

Provenance & Evidence