2,6-Dibromopyridine → 2-(6-Bromopyridin-2-yl)-4-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

2,6-Dibromopyridine (0.94 g, 4.0 mmol), 4-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile (1.48 g, 6.0 mmol) and potassium phosphate (1.70 g, 8.0 mmol) were dissolved in N,N-dimethylformamide (12 ml) and degassed with nitrogen for 15 min. Tetrakis(triphenylphosphine)palladium(0) (230 mg, 0.2 mmol) was added then the mixture heated at 80° C. for 16 h. The mixture was allowed to cool to ambient temperature, diluted with water (150 ml) and extracted into ethyl acetate (2×150 ml). The combined organics were washed with brine (100 ml), dried over anhydrous sodium sulfate and evaporated to give a yellow oil. Purification by flash column chromatography on silica eluting with isohexane on a gradient of ethyl acetate (10-15%) gave 4-fluoro-2-(6-bromopyridin-2-yl)benzonitrile (0.42 g, 38%) as a waxy solid: δH (360 MHz, CDCl3) 7.21-7.25 (1H, m), 7.59 (1H, d, J 8), 7.67 (1H, dd, J 9.3, 2.6), 7.72 (1H, t, J 7.7), 7.78-7.87 (2H, m).

Provenance & Evidence