1,3,5-Tribromobenzene → HCID 19889431, compound

Participants

Reaction Steps

Tetrakis-(triphenylphosphine)palladium (915 mG; 0.75 mM) was added to a stirred solution of 1,3,5-tribromobenzene (6.3 G; 20 mM) in 75 mL of anhydrous tetrahydrofuran under nitrogen at R.T. After stirring 5 mins., tetra n-butyl ammonium bromide (483 mG; 1.5 mM), followed by powdered potassium hydroxide (2.52 G, 45 mM) and 3-pyridyldiethyl borane (2.2 G; 15 mM) were added in that order. The resulting reaction mixture was heated to reflux 2 hrs., cooled, diluted with 100 mL of ethyl acetate, washed with 10×25 mL of sat'd. sodium chloride solution, and dried over anhyd. magnesium sulfate. Solvent removal, and purification on silica gel using ethyl acetate:hexane (2:3) mixture as solvent gave 1.9 G of 3-(3',5'-dibromophenyl)pyridine as a colorless oil boiling at 137°-139°/~1 mm, which slowly became a glassy solid.

Provenance & Evidence