Synthesis
GENERAL STEPS: 4'-Bromo-[1,1'-biphenyl]-4-ol (3.5 g, 14.11 mmol), 1-bromopentane (3.75 g, 21.05 mmol) and anhydrous potassium carbonate (4.9 g, 35.28 mmol) were suspended in 2-butanone (25 mL) under nitrogen protection. The reaction mixture was heated to reflux and kept for 8 hours. After completion of the reaction, it was cooled to room temperature and diluted with dichloromethane (50 mL). The insoluble salt was removed by filtration and the organic phase was washed sequentially with distilled water (50 mL) and saturated saline (50 mL). The organic layer was dried over anhydrous sodium sulfate and filtered and concentrated under reduced pressure to about 15 mL. The residue was washed with cold hexane (0 °C) to afford 4-bromo-4'-(pentyloxy)biphenyl (4.6 g, 94.3% yield) as a white solid.
References
[1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 196 - 208
[2] Chemistry Letters, 2010, vol. 39, # 5, p. 513 - 515
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1474 - 1477
[4] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
[5] Patent: US5948753, 1999, A
