4-Bromophenol → 3-(4-Hydroxyphenyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

3-Cyanophenylboronic acid (1.18 g, 8.03 mmol), 4-bromophenol (1.16 g, 6.69 mmol) and sodium carbonate (2.12 g, 20.07 mmol) were dissolved in dioxane (20 mL) and water (8 mL) and the reaction mixture was degassed under nitrogen. Tetrakistriphenylphosphinepalladium (0) (0.77 g, 0.67 mmol) was added and the reaction was stirred at 110° C. for 2 hours. The mixture was cooled to room temperature, filtered through pad of Arbocel™ and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (30 mL) and water (15 mL). The organic layer was dried over anhydrous magnesium sulphate, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in heptane to give the title compound as a pale yellow solid (0.58 g, 44%).

Provenance & Evidence