1: 12 percent / CuCl, K2CO3 / 2-ethoxy-ethanol / 6 h / Heating 2: 59 percent / polyphosphoric acid (PPA) / 1 h / 115 °C 3: 66 percent / K2CO3 / propan-2-ol / 2 h / Heating 4: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 5: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme

sodium methylate; copper(l) chloride 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h; Yield given. Multistep reaction;

1: 1.) NaOMe, 2.) CuCl / 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h 2: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating 3: 11 percent / 1.) n-BuLi, 2.) lithium salt of t-butylperoxide / 1.) n-hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min View Scheme

1: 1.) NaOMe, 2.) CuCl / 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h 2: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating 3: 5 percent / 1.) n-BuLi, 2.) lithium salt of t-butylperoxide / 1.) hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min View Scheme

1: 1.) NaOMe, 2.) CuCl / 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h 2: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating 3: 17 percent / 1.) n-BuLi, 2.) lithium salt of t-butylperoxide / 1.) n-hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min View Scheme

1: 1.) NaOMe, 2.) CuCl / 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h 2: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating 3: 11 percent / 1.) n-BuLi, 2.) lithium salt of t-butylperoxide / 1.) n-hexane, Et2O, 4 deg C, 48 h, 2.) -78 deg C -> RT, then reflux, 5 min 4: diethyl ether View Scheme

1: 1.) NaOMe, 2.) CuCl / 1.) MeOH,benzene, 2.) pyridine, reflux, 20 h 2: 46 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid / 2.3 h / Heating View Scheme

1: 1-bromo-2,3,5-trimethoxybenzene With n-butyllithium in diethyl ether; hexane T=-78°C; 1.5 h; 2: methyl iodide in diethyl ether; hexane T=-78 - 20°C; 1.5 h;