Phosphorus tribromide → 2-(Benzofuran-5-ylmethyl)pyridine

Participants

Reaction Steps

A solution of benzofuran-5-yl(pyridin-2-yl)methanol (500 mg, 2220 μmol) in DCM (10 mL) at 0° C. was treated with tribromophosphine (314 μL, 3330 μmol) and stirred for 1.5 h. The mixture was diluted with CHCl3, washed with sat. aqueous KHCO3, dried over MgSO4, and evaporated. A suspension of the crude material and 10% Pd—C (50 mg) in EtOAc (5 mL) and MeOH (3 mL) was stirred under 1 atm H2 at 24° C. for 1 h. The solids were filtered off (Celite) and washed with EtOAc. The filtrate was evaporated and purified by flash chromatography (hexanes to EtOAc to 5% MeOH in DCM) to give 2-(benzofuran-5-ylmethyl)pyridine as a yellow foam. 1H NMR (400 MHz, CD3OD) δ ppm 8.71 (br. s, 1H), 8.17 (t, J=7.6 Hz, 1H), 7.70-7.64 (m, 3H), 7.50-7.48 (m, 2H), 7.29 (d, J=8.1 Hz, 1H), 6.76 (s, 1H), 4.71 (s, 2H). MS (ESI) m/z: Calculated: 209.1; Observed: 210.0 (M++1).

Provenance & Evidence