Multi-step reaction with 14 steps
1: 79 percent / TiCl4 / CH2Cl2 / 1 h / 0 °C
2: 74 percent / BBr3 / CH2Cl2 / 1 h / 0 °C
3: 79.6 percent / K2CO3 / butan-2-one / 4.5 h / Heating
4: 82.9 percent / H2, conc.H2SO4 / 20percent Pd/C / acetic acid / 2 h / 2280 Torr
5: LiCl, Me2SO, H2O / 2 h / Heating
6: H2SO4 / Ambient temperature
7: 69.2 percent / AlCl3 / 1,2-dichloro-ethane / 3.75 h / 5 - 20 °C
8: 20 percent / NH2OH*HCl, pyridine / 4 h / Heating
9: 58 percent / 1 h / 90 °C
10: NaH / dimethylformamide / 4 h / Ambient temperature
11: 92 percent / aq. KOH / methanol / 1 h
12: SOCl2 / benzene / 2 h / Heating
13: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, from -78 to -30 deg C, 1.6 h
14: 79 percent / ethanolic KOH / tetrahydrofuran / 0.17 h / 5 °C
With
pyridine; potassium hydroxide; n-butyllithium; aluminium trichloride; thionyl chloride; sulfuric acid; hydroxylamine hydrochloride; water; hydrogen; boron tribromide; titanium tetrachloride; sodium hydride; potassium carbonate; dimethyl sulfoxide; lithium chloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; butanone; benzene;
DOI:10.1021/jm00374a014