Dichloromethane → 2-(6-Methoxy-2-naphthyl)-1-benzofuran

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-methoxy-2-bromonaphthalene (10.1 g, 42.6 mmol), 2-benzofuranboronic acid (8.28 g, 51.1 mmol), potassium carbonate (11.7 g, 84.8 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.887g, 1.09 mmol) in dioxane (420 mL) and water (42 mL) was heated to 69-72° C. for 2 hours. It was allowed to cool to room temperature and solvent evaporated. The residue was paroom temperatureitioned, with heating (because the product is very insoluble) in chloroform/2N hydrochloric acid. The organic phase was washed with water and brine. It was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 15-75% chloroform in hexane and 100% chloroform as eluants. It was dried for 30 minutes at 60° C. to afford 2-(6-methoxy-2-naphthyl)-1-benzofuran as a light yellow-brown solid (9.51 g, 81%): mp 194-195° C.; mass spectrum (+EI, M+) m/z 274. 1HNMR (400 MHz, DMSO-d6): δ8.4 (s, 1H), 7.9-8.0 (m, 3H), 7.65-7.7 (m, 2H), 7.5 (s, 1H), 7.35 (d, 1H, J=2.5 Hz), 7.2-7.35 (m, 3H), and 3.9 ppm (s, 3H). Elemental Analysis for C19H14O2: Calculated: C, 83.19; H, 5.14; N, 0.00; Found: C, 82.96; H, 4.98; N, 0.01;

Provenance & Evidence