cesium fluoride in tetrahydrofuran T=85°C; Suzuki-Miyaura reaction; 1.5 h; microwave irradiation;

potassium hydroxide in acetone Ambient temperature;

1.1: LHMDS / tetrahydrofuran / 2.5 h / -78 - -20 °C 1.2: tetrahydrofuran / 3 h / -78 - 20 °C 1.3: 75 percent / AcOH; H2SO4 / tetrahydrofuran / 0.08 h / 120 °C 2.1: 84 percent / POPd; CsF / tetrahydrofuran / 1.5 h / 85 °C / microwave irradiation View Scheme

1.1: LHMDS / tetrahydrofuran / 2.5 h / -78 - -20 °C 1.2: tetrahydrofuran / 3 h / -78 - 20 °C 1.3: 75 percent / AcOH; H2SO4 / tetrahydrofuran / 0.08 h / 120 °C 2.1: 84 percent / POPd; CsF / tetrahydrofuran / 1.5 h / 85 °C / microwave irradiation View Scheme

1: 3'-bromo-2'-hydroxychalcone With zinc(II) chloride in dichloromethane T=20°C; 12 h; 2: 3,4,5-trimethoxyphenylboronic acid With tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethylene glycol dimethyl ether Suzuki coupling; Inert atmosphereReflux; 3: With dihydrogen peroxide in tetrahydrofuran; water T=0°C; 1 h; regioselective reaction;

1: 90 percent / 60percent aq. KOH / ethanol / 3 h / 50 - 60 °C 2: 69 percent / Br2 / CCl4 / 0.5 h / Ambient temperature 3: 94 percent / 20percent aq. KOH / acetone / Ambient temperature View Scheme

1: 69 percent / Br2 / CCl4 / 0.5 h / Ambient temperature 2: 94 percent / 20percent aq. KOH / acetone / Ambient temperature View Scheme