Hydrochloric Acid → HCID 69410849, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1,6-dibromo-naphthalen-2-yloxy)-acetic acid ethyl ester (6.9 g, 18 mmol), benzothiophene-2-boronic acid (4.78 g, 26.8 mmol) in two portions, palladium (II) acetate (0.11 g, 0.49 mmol), potassium carbonate (6.2 g, 45 mmol), tetrabutylammonium bromide (5.8 g, 18 mmol) in water (90 mL) and THF (35 mL) was heated at 70° C. for 3.5 hours. The reaction mixture was allowed to cool to ambient temperature and then poured into excess 2N hydrochloric acid. It was extracted with chloroform. The organic phase was then washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered hot (due to limited solubility) and solvent evaporated. The residue was purified by flash chromatography using 25–45% methylene chloride in hexane and 100% chloroform as eluent. Drying at 60° C. in vacuo for 30 minutes yielded (6-benzo[b]thiophen-2-yl-1-bromo-naphthalen-2-yloxy)-acetic acid ethyl ester as a buff-colored solid (3.3 g, 42%) MP: 178–81° C.; mass spectrum (+EI, M+) m/z 440/442. 1H NMR (500 MHz, DMSO-d6): δ8.32 (d, 1H,J=1.83 Hz), 8.18 (d, 1H, J=8.86 Hz), 8.07–8.12 (m, 2H), 8.01 (d, 2H, J=7.33 Hz), 7.88 (dd, 1H, J=7.63 Hz and 1.07 Hz), 7.47 (d, 1H, J=9.16 Hz), 7.36–7.43 (m, 2H), 5.09 (s, 2H), 4.18 (q, 2H, J=7.08 Hz), 1.22 ppm (t, 3H, J=7.11 Hz). Elemental Analysis for C22H17BrO3S: Calcd: C, 59.87; H, 3.88; N, 0.00; Found: C, 60.03; H, 3.83; N, 0.00.

Provenance & Evidence