Uses
Employed as an important intermediate for raw material for organic synthesis, agrochemical, pharmaceutical and dyestuff field
Synthesis
The general procedure for the synthesis of 2-bromo-5-methoxybenzyl bromide from 2-bromo-5-methoxytoluene was as follows: 2-bromo-5-methoxytoluene (0.050 mol) and N-bromosuccinimide (NBS, 0.055 mol) were dissolved in carbon tetrachloride (125 mL), and azobisisobutyronitrile (AIBN, 0.001 mol) was added as initiator. The reaction mixture was stirred at 80 °C for 18 hours. Upon completion of the reaction, the mixture was diluted with hexane and subsequently filtered through a diatomaceous earth pad to remove insoluble impurities. The filtrate was concentrated under reduced pressure to remove the solvent and the residue was washed with ethyl acetate to give the final target product 4-bromo-3-(bromomethyl)anisole.
References
[1] Tetrahedron, 2004, vol. 60, # 49, p. 11075 - 11087
[2] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10124 - 10125
[3] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 4973 - 4983
[4] Synlett, 2011, # 17, p. 2525 - 2528
[5] Journal of Medicinal Chemistry, 2000, vol. 43, # 1, p. 22 - 26
