1: 1-bromo-2,4-dihydroxybenzene; p-toluenesulfonyl chloride With potassium carbonate in acetone Heating; 2: methyl iodide in acetone Heating;

potassium carbonate in acetone 3 h; Heating;

1: K2CO3 / acetone / 21 h / Heating 2: 79 percent / K2CO3 / acetone / 3 h / Heating View Scheme

1: K2CO3 / acetone / 14 h / Heating 2: acetone / 16 h / Heating View Scheme

1.1: 98 percent / PdCl2(PPh3)2; CuI; Et3N / dimethylformamide / 6 h / 100 °C 2.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2.2: 99 percent / H2O / tetrahydrofuran / 20 °C 3.1: 96 percent / CuI; PdCl2(PPh3)2; iPr2NH / dimethylformamide / 1 h / 60 °C 4.1: 98 percent / I2 / CH2Cl2 / 12 h / 25 °C 5.1: 60 percent / PdCl2(PPh3)2; K2CO3 / dimethylformamide / 6 h / 60 °C 6.1: 99 percent / n-Bu4N(1+)*F(1-) / dimethylformamide / 2 h / 100 °C View Scheme

sodium hydroxide in methanol 1.5 h; Heating;

1: 94 percent / KI; CuI / hexamethylphosphoric acid triamide / 3 h / 150 °C 2: 98 percent / CuI; Et3N / PdCl2(PPh3)2 / dimethylformamide / 1 h / 20 °C 3: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C 4: 96 percent / CuI; i-Pr2NH / PdCl2(PPh3)2 / dimethylformamide / 1.5 h / 60 °C 5: 81 percent / DIBAL-H / toluene; CH2Cl2 / 3 h / -78 °C 6: 67 percent / TBAF / tetrahydrofuran / 3 h / Heating 7: 78 percent / NaOMe / methanol / 20 h / Heating View Scheme