Diethyl Ether → 2-(2-Bromoethyl)pyridine

Participants

Reaction Steps

To a solution of 2-pyridineethanol (1.00 ml) in tetrahydrofuran (20 ml) were successively added triphenylphosphine (3.51 g) and carbon tetrabromide (4.44 g) with stirring at room temperature, and the resulting mixture was stirred at room temperature overnight. After stirring, to the reaction mixture was added diethyl ether, and insoluble materials were filtered off, and the organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (1:3) as the eluent to afford the title compound (1.30 g, yield: 78%) as a yellow oil.

Provenance & Evidence