1-Butanol → HCID 121409857, compound

Participants

Reaction Steps

One 100 mL round-bottomed flask was charged with 5-bromo-2-(2,4-difluorophenyl)pyridine (0.5 g, 1.851 mmol), 2-(4-chloro-2,6-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.730 g, 2.74 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-3-yl)phosphine (0.021 g, 0.044 mmol), diacetoxypalladium (8.31 mg, 0.037 mmol), and butanol (Volume: 6 ml) to give a yellow suspension. The reaction mixture was then stirred for 15 minutes at room temperature. Lithium hydroxide (0.075 g, 3.15 mmol) was added into reaction mixture and then heated to 80° C. for 1 hour. The reaction mixture was then diluted with deionized water and extracted by ethyl acetate. The organic portion was combined and subjected to column chromatography (SiO2 gel, 5% EtOAc in heptane) to yield the desired compound, 5-(4-chloro-2,6-dimethylphenyl)-2-(2,4-difluorophenyl)pyridine (0.525 g, 86%).

Provenance & Evidence