Hydrochloric Acid → HCID 21075903, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1-chloro-naphthalen-2-ol (11.2 g, 43.5 mmol), benzothiophene-2-boronic acid (15.1 g, 85.0 mmol) in three portions, palladium (II) acetate (0.76 g, 3.43 mmol) in three portions, potassium carbonate (30.1 g, 224 mmol) in three portions, tetrabutylammonium bromide (14.0 g, 43.5 mmol) in water (65 mL) and THF (40 mL) was heated at 70° C. for 8.5 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 and solvent evaporated. The residue was purified by flash chromatography using 100% chloroform, 30–50% 1,2-dichloroethane in hexane and 20–30% 1,2-dichloroethane in hexane (Biotage apparatus) eluent. Drying at 60° C. in vacuo for 20 minutes yielded 6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-ol as a beige-yellow solid (3.22 g, 23.9%) MP: 220–1° C.; Mass spectrum (−ES, [M−H]−) m/z 309/311. 1H NMR (500 MHz, DMSO-d6): δ 10.64 (s, 1H), 8.26 (d, 1H, J=1.73 Hz), 8.11 (d, 1H, J=8.85 Hz), 8.05 (dd, 1H, J=8.85 and 1.83 Hz), 7.95–8.01 (m, 2H), 7.87–7.92 (m, 2H), 7.33–7.43 ppm (m, 3H). Elemental Analysis for C18H11ClOS: Calcd: C, 69.56; H, 3.57; N, 0.00; Found: C, 69.58; H, 3.83; N, 0.00.

Provenance & Evidence