Boron trifluoride etherate → HCID 57445080, compound

Participants

Reaction Steps

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) and Ti(Oi-Pr)4 (9.05 mL, 27.5 mmol) in ether (100 mL) at −78° C. was added EtMgBr (18.3 mL, 55 mmol) dropwise. The solution was allowed to warm to room temperature and stirred for 1 hour before BF3-Et2O (6.25 mL) was added and stirring continued at room temperature for another 1 hour. The reaction solution was quenched with 1 N HCl solution, and washed with EtOAc. The aqueous layer was adjusted to pH˜10 with aq. NaOH (2 N) solution and then exacted with EtOAc (3×). The combined organic layers were dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The residue was then purified by column chromatography to give title compound (3.0 g, yield 52.2%) as yellowish oil.

Provenance & Evidence