potassium carbonate in acetone Methylation; 72 h; Heating;

boron tribromide in dichloromethane T=-70°C; 0.0833333 h;

1: silver trifluoroacetate,iodine / CHCl3 / 1 h / 20 - 25 °C 2: 85 percent / K2CO3 / acetone / 0.75 h / Heating 3: 97 percent / PPh3, CuI / PdCl2 / triethylamine; dimethylformamide / 0.8 h / 80 °C 4: 88 percent / K2CO3 / methanol / 0.8 h / Heating 5: 82 percent / BBr3 / CH2Cl2 / 0.08 h / -70 °C View Scheme

1: 89 percent / silver trifluoroacetate, iodine / CHCl3 / 1 h / 20 - 25 °C 2: 1.) BBr3; 2.) water / 1.) CH2Cl2, -70 deg C, 5 min; 2.) 1 h 3: 85 percent / K2CO3 / acetone / 0.75 h / Heating 4: 97 percent / PPh3, CuI / PdCl2 / triethylamine; dimethylformamide / 0.8 h / 80 °C 5: 88 percent / K2CO3 / methanol / 0.8 h / Heating 6: 82 percent / BBr3 / CH2Cl2 / 0.08 h / -70 °C View Scheme

1: 85 percent / K2CO3 / acetone / 0.75 h / Heating 2: 97 percent / PPh3, CuI / PdCl2 / triethylamine; dimethylformamide / 0.8 h / 80 °C 3: 88 percent / K2CO3 / methanol / 0.8 h / Heating 4: 82 percent / BBr3 / CH2Cl2 / 0.08 h / -70 °C View Scheme

1: 97 percent / PPh3, CuI / PdCl2 / triethylamine; dimethylformamide / 0.8 h / 80 °C 2: 88 percent / K2CO3 / methanol / 0.8 h / Heating 3: 82 percent / BBr3 / CH2Cl2 / 0.08 h / -70 °C View Scheme

1: 88 percent / K2CO3 / methanol / 0.8 h / Heating 2: 82 percent / BBr3 / CH2Cl2 / 0.08 h / -70 °C View Scheme

1: 40 percent / stannous chloride dihydrate / acetic acid; H2O / 4.5 h / Heating 2: 32 percent / pyridine / 18 h / Heating View Scheme

pyridine 18 h; Heating;