Ethyl bromoacetate → [1-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

Participants

Reaction Steps

Following the procedure described in Method B, Step 5 of Example 1, the title compound was prepared from 1-bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol (1.5 g, 3.66 mmol), cesium carbonate (2.4 g, 7.34 mmol), ethyl bromoacetate (0.48 mL, 4.3 mmol) in acetone (35 mL). The title compound was obtained as an off-white solid (1.6 g), mp 93-95° C. Mass spectrum (+APCl, [M+H]+) m/z 495. 1HNMR (300 MHz, DMSO-d6): δ8.34 (s, 1H), 8.24 (d, 1H, J=9.0 Hz), 8.12 (d, 1H, J=9.1 Hz), 8.06-8.02 (m, 1H), 7.69 (d, 1H, J=7.1 Hz), 7.61 (d, 1H, J=7.7 Hz), 7.48 (d, 1H, J=9.1 Hz), 7.37-7.26 (m, 2H), 5.1 (s, 2H), 4.18 (q, 2H, J=7.1 Hz), 3.01 (t, 2H, J=7.3 Hz), 1.76-1.64 (m, 2H), 1.43-1.26 (m, 4H), 1.22 (t, 3H, J=7.1 Hz), and 0.85-0.79 ppm (m, 3H). Elemental Analysis for C27H27BrO4.1.0H2O: Calculated: C, 63.16; H, 5.69; N, 0.00. Found: C, 62.90; H, 5.19; N, 0.15.

Provenance & Evidence