3-Phenoxybromobenzene

108-36-1

108-95-2

6876-00-2

Example 6 Synthesis of 1-bromo-3-phenoxybenzene (A): a mixture of meso-dibromobenzene (3 g, 12.75 mmol), phenol (1 g, 10.6 mmol), copper(I) oxide (152 mg, 1 mmol), and cesium carbonate (3.46 g, 10.6 mmol) was dissolved in 8 mL of N-methylpyrrolidone (NMP). The reaction mixture was microwaved at 195 °C for 20 min. Upon completion of the reaction, the non-homogeneous mixture was filtered through a bed of diatomaceous earth and the residue was washed with ethyl acetate (EtOAc, 1 × 20 mL). The filtrate was diluted with 1N sodium hydroxide solution (200 mL) and subsequently extracted with ethyl acetate (3 × 100 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product as a yellow oil. The crude product was purified by column chromatography (100% hexane as eluent) to afford 1-bromo-3-phenoxybenzene as a colorless oil (1.4 g, 53% yield).LCMS m/z 250 (M + 1).