lithium bromide; p-toluenesulfonic acid monohydrate; bromine; lithium carbonate in tetrachloromethane; chloroform; water; N,N-dimethyl-formamide; benzene

bromine in ethanol; chloroform

toluene-4-sulfonic acid 17 h; Heating;

bromine; sodium methylate; potassium acetate in tetrachloromethane; ethanol 2) reflux, 1h;

1: 85 percent / pyridine; ethanol / 22 h / Ambient temperature 2: 80 percent / KOH / methanol; H2O / 18 h / Heating 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

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

1: 89 percent / p-toluenesulfonic acid / 8 h / Heating 2: CaCO3, Br2, sodium thiosulfate, LiBr, Li2CO3, p-toluenesulfonic acid 3: 84.1 percent / pyridine; ethanol / 22 h / Ambient temperature 4: 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 5: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 6: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 7: KOH / methanol; H2O / 18 h / Heating 8: various solvent(s) / Heating 9: 2N HCl / acetone / 5 h / Heating 10: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 2N HCl / acetone / 5 h / Heating 2: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 2N HCl / acetone / 5 h / Heating 2: 87 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme