1: 1.) Mg / 1.) THF 2: 46.7 percent / 60 h / 145 °C View Scheme

sulfuric acid T=0°C; 2 h;

1: 75 percent / concd. H2SO4 / 2.5 h / 0 °C 2: 62 percent / 10percent Pd/C / diphenyl ether / 2.5 h / Heating 3: N-bromosuccinimide, AIBN / CCl4 / 6.5 h / Heating 4: NaI / acetone / 6 h / Heating View Scheme

1.1: magnesium; 2-monochloropropane / ethyl bromide; iodine; isopropylmagnesium chloride / tetrahydrofuran / 0 - 70 °C / Industry scale 1.2: 8.5 h / -5 - 55 °C / Industry scale 2.1: triethylsilane / dichloromethane / 20 °C / Industry scale 2.2: -5 - 20 °C / Industry scale 3.1: caesium carbonate / N,N-dimethyl-formamide; tetrahydrofuran / 0 - 25 °C / Industry scale View Scheme

1: 90 percent / KOH / Heating 2: 77 percent / POCl3 / 100 °C 3: 97 percent / AlCl3 / CH2Cl2 / 25 °C View Scheme

1: 1) NaH / 1) DMF, r.t., 2) r.t. 2: 1) phosphorus oxychloride / 1) 0 deg C, 2) 60 deg C View Scheme

sulfuric acid; benzene

1: 71 percent / KH2PO4; NO(KSO3)2 / methanol; H2O / 1.42 h / Cooling 2: 75 percent / Na2S2O4 / H2O View Scheme