2-(3-Bromo-4-methoxyphenyl)pyridine

Synthesis

N-bromosuccinimide (II) (108 mg, 0.6 mmol) was dissolved in N,N-dimethylformamide (0.2 M, 1.5 mL) as 2-(4-methoxyphenyl)pyridine (Ib) (56 mg, 0.3 mmol). 5-Cyclooctadiene ruthenium dichloride (8 mg, 10 mol%) was added as a catalyst and the reaction mixture was stirred at 150 °C for 24 hours. After completion of the reaction, the mixture was extracted with ethyl acetate (20 mL) and the organic phase was washed with water (10 mL x 3). The organic phase was dried with anhydrous sodium sulfate, filtered and the solvent was removed by rotary evaporator. The crude product was purified by column chromatography to afford 2-(3-bromo-4-methoxyphenyl)pyridine (III-b) (72 mg, colorless oil) in 90% yield.

References

[1] Angewandte Chemie - International Edition, 2015, vol. 54, # 50, p. 15284 - 15288
[2] Angew. Chem., 2015, vol. 127, # 50, p. 15499 - 15503,5
[3] Patent: CN104356053, 2017, B. Location in patent: Paragraph 0036; 0038; 0039