Ethanol → 3-Bromo-5-phenylpyridine

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium (577 mg; 0.5 mM) was added to 3,5-dibromopyridine (5.214 g; 22 mM) in 40 mL of toluene at R.T. under nitrogen. After 10 minutes stirring, 25 mL of 2M aqueous sodium carbonate solution, phenylboronic acid (2.44 g; 20 mM), and 10 mL of ethanol were added, and the mixture was heated 11 hours at 80° C. The reaction mixture was cooled, diluted with 75 mL of ethyl acetate and washed with 2×15 mL of saturated sodium carbonate solution, and then dried over anhydrous magnesium sulfate. Solvent removal gave crude product, which was chromatographed on silica gel using ethyl acetate:hexane (1:5) mixture to give a white solid boiling at 100°-101° C./~0.1 mm in 28% yield.

Provenance & Evidence