Multi-step reaction with 8 steps
1: 1.) n-BuLi / 1.) THF, -74 deg C, 30 min, 2.) THF, from -74 deg C to RT
2: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT
3: HCl(g) / 18 h / Ambient temperature
4: 41 percent / 30 h / 175 °C
5: 66 percent / K2CO3, KI, DMSO / butan-2-one / 18 h / Heating
6: H2 / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature
7: BBr3 / CH2Cl2 / 1 h / -78 °C
8: 100 percent / aq. NaOH / methanol; tetrahydrofuran / 1 h / Ambient temperature
With
hydrogenchloride; sodium hydroxide; n-butyllithium; hydrogen; boron tribromide; potassium carbonate; dimethyl sulfoxide; potassium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; butanone;
DOI:10.1021/jm00022a006