Potassium Carbonate → 4-[4-(9-Bromo-2-,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxy]-butyric acid methyl ester

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A solution of 2-cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol (0.30 g, 0.81 mmol), 4-bromobutyric acid, methyl ester (1.5 mL, 13.0 mmol), 60% sodium hydride (0.09 g, 2.3 mmol), potassium carbonate (1.0 g, 7.2 mmol), and anhydrous benzene (2 mL) was heated at 100° for 36 h. Purification by chromatography with hexanes/ethyl acetate gave the title compound as a solid (0.23 g, 52%): NMR (DMSO-d6): δ 8.18 (d, J=8 Hz, 1H), 7.62 (ddd, J=2,6,8 Hz, 1H), 7.50-7.41 (m, 2H), 7.16-7.04 (m, 3H), 4.11 (m, 2H), 3.63 (s, 3H), 3.31 (quintet, J=8 Hz, 1H), 2.57 (t, J=7 Hz, 2H), 2.42 (s, 3H), 2.07 (quintet, J=7 Hz, 2H), 1.95 (m, 2H), 1.74-1.45 (m containing a singlet at δ 1.56, 9H); MS(EI): [M+], 1 bromine isotope pattern, 550/552.

Provenance & Evidence