Synthesis
Example 3.1 Synthesis of 1-bromo-4-(hexyloxy)benzene: Increase the temperature of the oil bath to 65 °C. In a 500 mL round-bottomed flask fitted with a stirrer, 10 g (57.8 mmol, 1.0 eq.) of 4-bromophenol and 26.36 g (190.7 mmol, 3.3 eq.) of potassium carbonate were added sequentially, followed by 202.3 mL of acetone. The reaction vessel was sealed, a condenser tube was fitted and purged continuously with argon for 10 min. After completion of the purge, 8.9 mL (64 mmol, 1.1 eq.) of bromohexane was slowly added via syringe, and the reaction mixture was stirred under reflux conditions in an oil bath for 24 hours. The progress of the reaction was monitored by thin layer chromatography (silica gel plate, hexane as the unfolding agent) and after confirming the completion of the reaction, the crude reaction mixture was filtered to remove potassium carbonate. Water was added to the filtrate and extracted twice with ether. The ether extracts were combined and dried with magnesium sulfate, followed by filtration to remove the desiccant. The solvent was removed by distillation under reduced pressure and the crude product obtained was purified by silica gel column chromatography (eluent hexane) to give 13.96 g (93.9% yield) of the target product 1-bromo-4-(hexyloxy)benzene as a clear liquid.GC-MS analysis showed the correct molecular ion peaks.1H NMR (500 MHz, CDCl3, internal standard TMS, δ 7.26 ppm): δ 7.355 (m, 2H), 6.770 (m, 2H), 3.912 (t, J = 6.75 Hz, 2H), 1.764 (m, 2H), 1.49-1.40 (m, 2H), 1.37-1.30 (m, 4H), 0.905 (t, J = 7.0 Hz, 3H).
References
[1] Angewandte Chemie - International Edition, 2014, vol. 53, # 12, p. 3168 - 3172
[2] Angew. Chem., 2014, vol. 126, # 12, p. 3232 - 3236,5
[3] European Journal of Organic Chemistry, 2013, # 26, p. 5917 - 5922
[4] Chemistry - A European Journal, 2017, vol. 23, # 17, p. 4149 - 4159
[5] Helvetica Chimica Acta, 2009, vol. 92, # 6, p. 1023 - 1033
