Phosphorus tribromide → 2-(Bromomethyl)-6-methylpyridine

Participants

Reaction Steps

(6-methyl-2-pyridinyl)methanol (ALDRICH, 300 mg, 2.436 mmol) were dissolved in 10 mL of anhydrous THF. Phosphorous tribromide (ALDRICH, 0.252 mL, 2.68 mmol) was added. Reaction mixture was stirred at room temperature overnight. Solvent was evaporated and residue was purified by silica column chromatography using hexane:EtOAc as eluents to give a white solid. This solid was partitioned between EtOAc and distilled water (basified with NH3 (32%, aqueous). Organic layer was dried with MgSO4 (anh). Solvent was evaporated to obtain the title compound (152 mg, 0.817 mmol, 33.5% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 7.68 (t, 1H), 7.33 (d, 1H), 7.17 (d, 1H), 4.62 (s, 2H), 2.44 (s, 3H). [ES+MS] m/z 186 (M).

Provenance & Evidence