Phenol → HCID 13266144, compound

Participants

Reaction Steps

2-(4-Bromophenoxy)-phenol was prepared by reported method. A mixture of phenol (2.65 g, 10.0 mmol) and K2CO3 (1.45 g, 10.5 mmol) in DMF (20 mL) was stirred for 0.5 hours, and then benzylbromide (1.56 mL, m 13.0 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours, then was diluted with ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, 2 N HCl, sat'd NaHCO3, and brine, dried under anhydrous MgSO4, filtered, and dried under reduced pressure. The residue was purified by column chromatography to give the desired product as a white solid (3.00 g, 84%). 1H NMR (500 MHz, CDCl3) δ 5.06-5.13 (m, 2H), 6.85 (d, J=9.0 Hz, 2H), 7.00 (t, J=9.0 Hz, 1H), 7.05-7.23 (m, 5H), 7.26-7.37 (m, 3H), 7.42 (d, J=9.0 Hz, 2H); 13C NMR (126 MHz, CDCl3) δ 70.6, 114.6, 115.3, 118.6, 121.9, 122.4, 125.7, 127.2, 128.0, 128.6, 132.5, 136.8, 144.9, 150.7, 157.9;

Provenance & Evidence