Multi-step reaction with 8 steps
1: 25.2 g / H2 / 10percent Pd/C / ethanol; H2O / 3 h / 760 Torr / Ambient temperature
2: 82 percent / 48percent aq. HBr / toluene / 2 h / Heating
3: 74 percent / KNO3, H2SO4 / 4 h / Ambient temperature
4: 98 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature
5: 1.) n-BuLi / 1.) THF, 0 deg C, 90 min, 2.) THF, a) -78 deg C, 90 min, b) 0 deg C, 2 h
6: HCl, AcOH / 9 h / Heating
7: SOCl2 / 6 h / Ambient temperature
8: CH2Cl2 / 36 h / Ambient temperature
With
hydrogenchloride; n-butyllithium; thionyl chloride; sulfuric acid; hydrogen bromide; hydrogen; sodium hydride; acetic acid; potassium nitrate;
palladium on activated charcoal;
In
ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja953578v