1: CaCO3, Br2, sodium thiosulfate, LiBr, Li2CO3, p-toluenesulfonic acid 2: 84.1 percent / pyridine; ethanol / 22 h / Ambient temperature 3: 85.9 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C / 1) 0-5 deg C, 1.5h, 2) 15 min 4: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 5: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 6: KOH / methanol; H2O / 18 h / Heating 7: various solvent(s) / Heating 8: 2N HCl / acetone / 5 h / Heating 9: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 2: KOH / methanol; H2O / 18 h / Heating 3: various solvent(s) / Heating 4: 2N HCl / acetone / 5 h / Heating 5: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: various solvent(s) / Heating 2: 2N HCl / acetone / 5 h / Heating 3: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 2: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 3: KOH / methanol; H2O / 18 h / Heating 4: various solvent(s) / Heating 5: 2N HCl / acetone / 5 h / Heating 6: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 80 percent / KOH / methanol; H2O / 18 h / Heating 2: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 3: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 4: KOH / methanol; H2O / 18 h / Heating 5: various solvent(s) / Heating 6: 2N HCl / acetone / 5 h / Heating 7: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 74 percent / p-toluenesulfonic acid / 18 h / Heating 2: 89 percent / p-toluenesulfonic acid / 8 h / Heating 3: CaCO3, Br2, sodium thiosulfate, LiBr, Li2CO3, p-toluenesulfonic acid 4: 84.1 percent / pyridine; ethanol / 22 h / Ambient temperature 5: 85.9 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C / 1) 0-5 deg C, 1.5h, 2) 15 min 6: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 7: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 8: KOH / methanol; H2O / 18 h / Heating 9: various solvent(s) / Heating 10: 2N HCl / acetone / 5 h / Heating 11: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 84.1 percent / pyridine; ethanol / 22 h / Ambient temperature 2: 85.9 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C / 1) 0-5 deg C, 1.5h, 2) 15 min 3: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 4: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 5: KOH / methanol; H2O / 18 h / Heating 6: various solvent(s) / Heating 7: 2N HCl / acetone / 5 h / Heating 8: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

2: 85 percent / pyridine; ethanol / 22 h / Ambient temperature 3: 80 percent / KOH / methanol; H2O / 18 h / Heating 4: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 5: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 6: KOH / methanol; H2O / 18 h / Heating 7: various solvent(s) / Heating 8: 2N HCl / acetone / 5 h / Heating 9: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

lithium carbonate; lithium bromide in N,N-dimethyl-formamide 0.5 h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

lithium carbonate; toluene-4-sulfonic acid; lithium bromide 1) DMF, reflux, 0.5h, 2) ethanol, reflux, 18h; Yields of byproduct given;