Potassium Hydroxide → [1-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid

Participants

Reaction Steps

Following the procedure described in Step 4 of Example 6, [1-bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (1.25 g, 2.53 mmol), was hydrolyzed with potassium hydroxide (0.70 g, 12.5 mmol) in THF (30 mL) and water (10 mL). Crystallization from ethyl acetate/hexane furnished the title compound as an off-white solid (0.90 g), mp 159-161° C. Mass spectrum (+APCl, [M+H]+) m/z 467. 1HNMR (400 MHz, DMSO-d6): δ13.2 (br s, 1H), 8.32 (d, 1H, J=1.5 Hz), 8.22 (d, 1H, J=9.0 Hz), 8.10 (d, 1H, J=9.0 Hz), 8.03 (dd, 1H, J=9.0, 1.5 Hz), 7.69-7.67 (m, 1H), 7.61 (d, 1H, J=8.0 Hz), 7.45 (d, 1H, J=9.0 Hz), 7.35-7.28 (m, 2H), 5.00 (s, 2H), 3.00 (t, 2H, J=7.8 Hz), 1.75-1.66 (m, 2H), 1.40-1.27 (m, 4H), and 0.84-0.79 ppm (m, 3H). Elemental Analysis for C25H23BrO2.1.0H2O: Calculated: C, 61.86; H, 5.19; N, 0.00. Found: C, 61.87; H, 4.70; N, 0.04.

Provenance & Evidence