Bromine → 1-Bromo-6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol

Participants

Reaction Steps

Following the procedure described in Step 4 of Example 1, 6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol (3.3 g, 10.0 mmol) was brominated using bromine (0.6 mL, 11.8 mmol), and potassium acetate (1.0 g. 10.2 mmol) in glacial acetic acid (40 mL). Purification by chromatography on a Biotage apparatus using 5% % ethyl acetate in hexane as the mobile phase furnished the title compound as an off-white solid (3.6 g), mp 75-77° C. Mass spectrum (+APCl, [M+H]+) m/z 409. 1HNMR (300 MHz, DMSO-d6): δ10.76 (br s,1H), 8.25 (d, 1H, J=1.2 Hz), 8.14 (d, 1H, J=8.9 Hz), 7.98-7.92 (m, 2H), 7.68-7.58 (m, 2H), 7.35-7.27 (m, 3H), 2.98 (t, 2H, J=7.3 Hz), 1.71 (p, 2H, J=6.9 Hz), 1.42-1.27 (m, 4H), and 0.87-0.80 ppm (tm 3H). Elemental Analysis for C23H21BrO2.0.7H2O: Calculated: C, 65.47; H, 5.35; N, 0.00. Found: C, 65.17; H, 4.92; N, 0.08.

Provenance & Evidence