General Description
4-Bromo-2-methylanisole can be prepared by the bromination of
o-methylanisole (2-methylanisole). It can also be prepared via reaction between 1-butyl-3-methylimidazolium tribromide [(Bmim)Br
3] and an activated aromatic compound. It participates as a substrate for the a-arylation of sulphonamide in a study.
Synthesis
General procedure for the synthesis of 2-methyl-4-bromoanisole from 2-methylanisole: In a dry 45 mL reaction tube equipped with a magnetic stirrer (note: air was not removed from the reaction tube), 1 mL of [Bmim]NO3, 0.5 mmol of 2-methylanisole and 0.25 mmol of Br2 were added. The reaction tube was then sealed and the reaction was carried out at 80 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was terminated by the addition of 3 mL of water. The target product 2-methyl-4-bromoanisole was extracted with dichloromethane (3 x 10 mL). The reaction mixture was analyzed by gas chromatography (GC) to determine the GC yield of the product. In another parallel experiment, the product was purified by column chromatography and structurally characterized using 1H NMR and 13C NMR.
References
[1] Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1068 - 1077
[2] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[3] Chemistry - A European Journal, 2015, vol. 21, # 34, p. 11976 - 11979
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 603 - 604
