Dichloromethane → HCID 18182814, compound

Participants

Reaction Steps

Following the procedure described in Step 1 of Example 1, ethyl 2-[(6-bromo-1-chloro-2-naphthyl)oxy]acetate (3.79 g, 11.0 mmol) and 2-benzofuranboronic acid (2.14 g, 13.2 mmol) were coupled in the presence of [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (1:1) (0.534 g, 0.654 mmol) and potassium carbonate (3.07 g, 22.2 mmol) in dioxane (110 mL) and water (11 mL). Purification by flash chromatography using 2-5% ethyl acetate in hexane as an eluant furnished ethyl 2-{[6-(1-benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetate as a cream-colored solid (1.91 g), mp 140-142° C. 1HNMR (300 MHz, DMSO-d6): δ8.5 (s, 1H), 8.2 (s, 2H), 8.1 (d, 1H, J=8.3 Hz), 7.75-7.85 (m, 2H), 7.7 (s, 1H), 7.5 (d, 1H, J=8.3 Hz), 7.25-7.4 (m. 2H), 5.1 (s, 2H), 4.2 (q, 2H, J=7.5 Hz), and 1.25 ppm (t, 2H, J=7.5 Hz).

Provenance & Evidence