Potassium Carbonate → 2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylsulfanyl]-benzofuran

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Reaktionsschritte

A mixture of 2-[1,2,3]thiadiazol-4-yl-phenol (241 mg, 1.35 mmol, 1 eq, prepared according to M. A. Abramov, W. Dehaen, B. D'hooge, M. L. Petrov, S. Smeets, S. Toppet and M. Voets Tetrahedron, 2000, 56, 3933-3940), 2-(4-bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (406 mg, 1.37 mmol, 1 eq), and potassium carbonate (396 mg, 2.87 mmol, 1.9 eq) was dissolved in 8 mL of acetonitrile and heated to 90° C. under a nitrogen atmosphere. After the reaction was complete as monitored by TLC, the mixture was filtered and the solvent removed in vacuo. The resulting crude material was chromatographed on silica gel eluting with 20% ethyl acetate/hexane to give 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylsulfanyl]-benzofuran (198 mg) in 40% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.3 (s, 12 H) 4.1 (s, 2 H) 6.6 (d, J=1.0 Hz, 1 H) 7.2 (m, 4 H) 7.4 (d, J=7.8 Hz, 2 H) 7.7 (d, J=8.1 Hz, 2 H).

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