Uses
2,3,4-(Trimethoxy)bromobenzene can be prepared from 1,2,3-(trimethoxy)benzene via bromination.
General Description
2,3,4-(Trimethoxy)bromobenzene can be prepared from 1,2,3-(trimethoxy)benzene via bromination.
Synthesis
General procedure for the synthesis of 2,3,4-tris(methoxy)bromobenzene from 1,2,3-trimethoxybenzene: In a dry 45 mL reaction tube equipped with a magnetic stirrer (note: the air inside the reaction tube is not displaced), 1 mL of [Bmim]NO3 as solvent, 0.5 mmol of 1,2,3-trimethoxybenzene, and 0.25 mmol of Br2 were added. The reaction tube was then sealed and the reaction was stirred at 80 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with 3 mL of water. The reaction mixture was extracted with dichloromethane (3 x 10 mL) to isolate the target product 2,3,4-tris(methoxy)bromobenzene. The GC yield of the product was determined by gas chromatography (GC) analysis. In another parallel experiment, the product was purified by column chromatography and structurally characterized using 1H NMR and 13C NMR.
References
[1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] Australian Journal of Chemistry, 1992, vol. 45, # 12, p. 1967 - 1982
[3] Journal of Chemical Research - Part S, 1998, # 10, p. 662 - 663
[4] Russian Journal of Organic Chemistry, 2007, vol. 43, # 9, p. 1282 - 1284
[5] Synthetic Communications, 2005, vol. 35, # 14, p. 1947 - 1952
