General procedure for the synthesis of 3-phenoxybromopropane (26) from 1,3-dibromopropane and phenol: Phenol (1.0 g, 10.6 mmol) was dissolved in acetone (20 ml). To this solution anhydrous potassium carbonate (7.34 g, 53.1 mmol) and 1,3-dibromopropane (8.58 g, 42.5 mmol) were added. The reaction mixture was refluxed in an oil bath for 12 hours. Upon completion of the reaction, the potassium carbonate was removed by filtration and the solvent was subsequently removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography (eluent: ethyl acetate:hexane = 3:7) to give the final target product 26 (2.05 g, 90% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 2.24 (m, 2H), 3.54 (t, J=6.4 Hz, 2H), 4.03 (t, J=5.8 Hz, 2H), 6.86 (m, 3H), 7.21 (m, 2H).
