potassium carbonate in acetone T=20°C; 5 h;

1: 56 percent 2: p-toluenesulfonic acid / Heating 3: 1) CaCO3, Br2, 2) Li2CO3, / 1) CCl4, water, 0-5 deg C, 30 min, 2) DMF, 30 min, reflux View Scheme

(i), (ii) (hydrolysis), (iii) (decarboxylation); Multistep reaction;

1: 56 percent 2: p-toluenesulfonic acid / Heating 3: 1) CaCO3, Br2, 2) Li2CO3, / 1) CCl4, water, 0-5 deg C, 30 min, 2) DMF, 30 min, reflux 4: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 5: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 6: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 7: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 8: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 9: 84 percent / various solvent(s) / Heating 10: 90 percent / 2N HCl / acetone / 5 h / Heating 11: 94.9 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

potassium carbonate in acetone 4 h; Heating;

1: (i) NaH, THF, (ii) /BRN= 774156/ 2: methanol View Scheme

1: 50 percent / t-BuOK / tetrahydrofuran / 50 h / 0 - 20 °C 2: 57 percent / HBr / 4 h / Heating View Scheme

sodium iodide in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=165 - 170°C;

1: 56 percent 2: p-toluenesulfonic acid / Heating 3: 1) CaCO3, Br2, 2) Li2CO3, / 1) CCl4, water, 0-5 deg C, 30 min, 2) DMF, 30 min, reflux 4: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 5: 2N HCl / acetone / 5 h / Heating View Scheme