Bromine → 1-[2-(8-Bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

Participants

Reaction Steps

Following the procedure described in Step 4 of Example 1, 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone (0.863 g, 2.51 mmol) was brominated using bromine (0.15 mL, 2.9 mmol), and potassium acetate (2.45 g. 25.0 mmol) in glacial acetic acid (25 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant followed by chromatography on a Biotage apparatus using 15-20% chloroform in hexane as an eluant furnished 1-[2-(8-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone as an orange solid (0.623 g), mp 160-161° C. 1HNMR (200 MHz, DMSO-d6): δ10.95 (s,1H), 8.4 (s, 1H), 8.2 (d, 1H, J=8.6 Hz), 7.9-8.1 (m, 3H), 7.7-7.8 (d, 1H, J=6.8 Hz), 7.3-7.55 (m, 3H), 2.8 (d, 1H, J=6.8 Hz), 2.0-2.2 (m, 1H), and 0.75 ppm (d, 6H, J=6.3 Hz).

Provenance & Evidence