Dichloromethane → 2-{[6-(1-Benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetonitrile

Participants

Reaction Steps

Following the procedure described in Step 1 of Example 1, 2-[(6-bromo-1-chloro-2-naphthyl)oxy]acetonitrile (9.7, 33 mmol) was coupled to 2-benzofuranboronic acid (6.35 g, 39 mmol), in the presence of[1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (1:1) (1.40 g, 1.71 mmol) and potassium carbonate (9.13 g, 66.1 mmol) in dioxane (330 mL) and water (3.3 mL). Purification by flash chromatography using 5-30% ethyl acetate in hexane and 7.5-50% ethyl acetate in hexane as eluants yielded 2-{[6-(1-benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetonitrile as a light brown solid (6.13 g), mp 162-163° C. 1HNMR (300 MHz, DMSO-d6): δ8.55 (s, 1H), 8.15-8.25 (m, 3H), 7.65-7.75 (m, 3H), 7.6 (s, 1H), 7.25-7.4 (m, 2H), and 5.45 ppm (s, 2H).

Provenance & Evidence