Dichloromethane → HCID 22482354, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 2-bromo-5-fluoroacetophenone (11.72 g, 54 mmol) and 2-fluorophenylboronic acid (7.55 g, 54 mmol) in tetrahydrofuran (600 mL) was treated under nitrogen with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (2.20 g, 2.69 mmol, 5 mole %) and a 5 N sodium hydroxide solution (21.6 mL, 108 mmol). The reaction was heated at 60° C. for twelve hours, cooled to room temperature, and the solvent removed in vacuo. The residue was dissolved in diethyl ether, filtered through a short column of silica gel, and the solvent evaporated in vacuo to a crude brown oil (11.72 g). The crude oil was purified by repetitive, preparative, liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with a gradient of between 3% and 10% methyl tert-butylether in hexane at a flow rate of 50 mL/min to afford, after evaporation of the solvent, the title compound as a purified, colorless oil (10.2 g, 43.9 mmol, 81%).

Provenance & Evidence