Multi-step reaction with 13 steps
1: 12.29 g / conc. HCl, H2 / Pd/C / ethanol / 70 °C / 3102.9 Torr
2: 96 percent / 1 M NaOH / tetrahydrofuran / 2 h / Heating
3: AlCl3 / CS2 / 70 °C
4: 3 M KOH
5: aq. HCl, NaNO2 / 0.5 h / 0 °C
6: K2CO3 / 0.5 h / 0 °C
8: 99 percent / MeI / 120 °C
9: 90 percent / Pd(dba)2, Ph3P, CuI, i-Pr2NH / tetrahydrofuran / 24 h
10: 96 percent / MeI / 120 °C
11: 76 percent / Pd(dba)2, Ph3P, CuI, i-Pr2NH / tetrahydrofuran / 120 h
12: 100 percent / K2CO3 / methanol; CH2Cl2
13: 50 percent / Pd(dba)2, Ph3P, CuI, i-Pr2NH / tetrahydrofuran / 120 h
With
hydrogenchloride; potassium hydroxide; sodium hydroxide; copper(l) iodide; aluminium trichloride; hydrogen; potassium carbonate; diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0); sodium nitrite; methyl iodide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; carbon disulfide; ethanol; dichloromethane;
DOI:10.1021/jo962336q