Synthesis
To a pre-dried 300 mL three-necked flask under nitrogen atmosphere were added 8-methylquinoline (10.0 g, 69.8 mmol), benzoyl peroxide (0.843 g, 3.49 mmol) and cyclohexane (150 mL). Under stirring conditions, N-bromosuccinimide (13.6 g, 76.8 mmol) was added in batches. The reaction mixture was refluxed for 10 hours. After completion of the reaction, the reaction mixture was filtered. The filtrate was washed sequentially with saturated aqueous sodium bicarbonate (3 x 100 mL) and brine (100 mL) and then dried with anhydrous sodium sulfate. Subsequently, the solvent was removed by vacuum evaporation. Finally, recrystallization was carried out using ether and hexane to give the light brown solid product 8-bromomethylquinoline (7.1 g, 46% yield).
References
[1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 1 - 9
[2] Journal of Organometallic Chemistry, 1994, vol. 484, # 1-2, p. C8 - C9
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1995, # 13, p. 2289 - 2296
[4] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 4, p. 477 - 479
[5] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 2109 - 2116
