(5-Bromo-3-pyridinyl)(phenyl)methanol

(5-Bromo-3-pyridinyl)(phenyl)methanol

n-Butyl lithium (17 ml, 2.5M in hexanes, 42.5 mmol) was added dropwise to cooled (−78° C.) solution of 3,5-dibromopyridine (10 g, 42.2 mmol) in ether (200 ml), so as to maintain an internal temperature <−70° C. The mixture was then stirred for 15 minutes and a solution of benzaldehyde (4.5 g, 42.5 mmol) in ether (20 ml) was added dropwise, again maintaining the temperature <−70° C. The mixture was stirred for 15 minutes, then allowed to warm to room temperature over an hour. The reaction was quenched by the addition of 0.9M ammonium chloride solution (200 ml), the layers separated, and the aqueous phase extracted with ether. The combined organic extracts were dried (MgSO₄) and evaporated under reduced pressure. The residual yellow oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane:ether (95:5 to 80:20) to give the title compound as a yellow oil, 7.6 g, 68%; 

¹H NMR (D₂O, 300 MHz) δ: 5.80 (s, 1H), 7.37 (m, 5H), 7.90 (s, 1H), 8.40 (s, 1H), 8.44 (s, 1H).