Synthesis
General procedure for the synthesis of 4-bromo-3,5-dimethylphenol from 3,5-dimethylphenol: To a mixture of 3,5-dimethylphenol (0.7 mmol) was added a dichloromethane (30 mL)-methanol (15 mL) solution of brominating agent (1) (0.72 g, 0.7 mmol). The reaction mixture was stirred at room temperature until the orange solution faded. The progress of the reaction was monitored by thin layer chromatography (TLC) (eluent: hexane/ethyl acetate, 7:3). After completion of the reaction, the solvent was evaporated and ether (10 mL) was added to the residue. The supernatant was decanted and the insoluble residue was washed with ether (3 x 10 mL). The ether extracts were combined, dried with magnesium sulfate, and the solvent was evaporated under vacuum to obtain the crude 4-bromo-3,5-dimethylphenol. The target product was purified by silica gel fast column chromatography (eluent: hexane/ethyl acetate, 7:3).
References
[1] Canadian Journal of Chemistry, 2009, vol. 87, # 2, p. 440 - 447
[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 11, p. 4187 - 4189
[3] Synlett, 2011, # 15, p. 2265 - 2269
[4] Journal of the Iranian Chemical Society, 2016, vol. 13, # 11, p. 2019 - 2028
[5] Tetrahedron, 2007, vol. 63, # 34, p. 8242 - 8249
