Hydrochloric Acid → HCID 21075902, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1,6-dibromo-naphthalen-2-yloxy)-acetonitrile (9.2 g, 27 mmol), benzothiophene-2-boronic acid (7.2 g, 40 mmol) in two portions, tetrabutylammonium bromide (8.7 g, 27 mmol), potassium carbonate (9.4 g 68 mmol) and palladium (II) acetate (0.079 g, 0.35 mmol) in THF (25 mL) and water (41 mL) was heated at 70° C. for seven hours. After cooling to ambient temperature, the reaction mixture was poured into 2N hydrochloric acid. This was extracted with hot chloroform (due to limited solubility). The organic phase was washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtrered and solvent evaporated. The residue was stirred in acetonitrile for ten minutes. It was then filtered and rinsed with acetonitrile. The precipitate was dried for 12 hours in vacuo at 76° C. to yield 6.8 g of title compound as a taupe-colored solid. The filtrate was concentrated and purified by flash chromatography with 10–45% chloroform in hexane. After drying for 20 minutes in vacuo at 60° C., 1.33 g more of the title compound was obtained as a light buff-colored solid. The total yield of (6-benzo[b]thiophen-2-yl-1-bromo-naphthalen-2-yloxy)-acetonitrile was 8.1 g (86%): MP: 179–81° C.; Mass spectrum (+EI, M+) m/z 393/395. 1H NMR (500 MHz, DMSO-d6): δ8.37 (d, 1H,J=1.83 Hz), 8.20 (d, 2H, J=7.94 Hz), 8.15 (dd, 1H, J=8.86 and 1.87 Hz), 8.01–4 (m, 2H), 7.88–7.90 (m, 1H), 7.67 (d, 1H, J=9.16 Hz), 7.37–7.43 (m, 2H), 5.44 ppm (s, 2H). Elemental Analysis for C20H12BrNOS: Calcd: C, 60.92; H, 3.07; N, 3.55; Found: C, 60.75; H, 2.91; N, 3.34.

Provenance & Evidence