Phosphorus tribromide → HCID 86680628, compound

Participants

Reaction Steps

To a stirred solution of 1-(5-(4-methoxyphenyl)pyridin-2-yl)ethanol (0.2 g, 0.8 mmol) in chloroform (4 mL) was added PBr3 (0.3 mL, 1.3 mmol) at 0° C. and the reaction was stirred at 0° C. to rt for about 1 h. The reaction mixture was quenched with saturated NaHCO3 solution (10 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120μ) using 10% ethyl acetate in hexane eluent to provide 2-(1-bromoethyl)-5-(4-methoxyphenyl)pyridine (0.15 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.76 (d, 1H), 7.84 (dd, 1H), 7.51 (dd, 3H), 7.01 (d, 2H), 5.32-5.26 (m, 1H), 3.86 (s, 3H), 2.11 (d, 3H), LC-MS m/z calcd for [M+H]+ 292.0. found 292.3.

Provenance & Evidence