Bromine → 2(4-Dibromomethylphenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

In a 100 ml four neck flask were placed 2-(4-tolyl)pyridine (5.0 g, 29.6 mmol) and chlorobenzene (18 ml), and bromine (9.4 g, 59.1 mmol) was added dropwise while heating the mixture at 110-120 ° C. over 12 hours. The reaction mixture was stirred with heating at a temperature in the above-mentioned range for 1 hour and analyzed by HPLC. As a result, 2-(4-bromomethylphenyl)pyridine was confirmed to have been produced in a 60.7% yield. The obtained reaction mixture was cooled and the precipitated 2-(4-bromomethylphenyl)pyridine salt was collected by filtration. The filtrate was neutralized with 5% aqueous sodium hydroxide solution. After washing with water, the mixture was dried over anhydrous magnesium sulfate. Chlorobenzene was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography (eluent: ethyl acetate-hexane) to give 2-(4-dibromomethylphenyl)pyridine in a 1.2 g yield. From the 1H-NMR analysis, the product was found to be 2-(4-dibromomethylphenyl)pyridine. 2-(4-dibromomethylphenyl)pyridine 1H-NMR(CDCl3, ppm) δ: 6.70(s,1H), 7.23-7.29(m,1H), 7.66-7.68(d,2H), 7.68-7.78(m,2H), 7.98-8.01(d,2H), 8.69-8.71(m,1H)

Provenance & Evidence