Multi-step reaction with 9 steps
1: 80 percent / NaNO2, conc. H2SO4 / 0.5 h / 0 °C
2: 75 percent / POCl3, pyridine / chlorobenzene / 1 h / Heating
3: 90 percent / Et3N / 144 h / Heating
4: 95 percent / H2 / 10percent Pd/C / ethanol / 760 Torr
5: 95 percent / Et3N / diethyl ether / 1 h / Ambient temperature
6: 1.) n-BuLi, tetramethylethylenediamine, 2.) I2 / 1.) THF, hexane, a) -78 deg C, 15 min, b) -25 deg C, 45 min, 2.) THF, hexane, a) -78 deg C, 15 min, b) -25 deg C, 3 h
7: 80 percent / BBr3 / CH2Cl2 / 10 h / Ambient temperature
8: 91 percent / pyridine / 25 h / Ambient temperature
9: 85 percent / K2CO3, Pd(PPh3)4 / toluene; ethanol / 2 h / 110 °C
With
pyridine; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; hydrogen; iodine; boron tribromide; potassium carbonate; triethylamine; sodium nitrite; trichlorophosphate;
palladium on activated charcoal;
In
diethyl ether; ethanol; dichloromethane; chlorobenzene; toluene;
DOI:10.1002/jhet.5570330670