Multi-step reaction with 7 steps
1: 70 percent / conc. H2SO4 / 0.33 h / 0 °C
2: 94 percent / NBS / CH2Cl2 / 0 °C
3: BF3*OEt2 / 0.83 h / 0 °C
4: 1.) NaOMe; 2.) imidazole / 1.) methanol, 0 degC, 40 min; 2.) DMF, room t., 2 h
5: 1.) n-BuLi; 2.) HClO4 / 1.) THF, hexane, -78 degC, 1 h; 2.) ether, AcOEt, water, room t., 5 min
6: 86 percent / CuCl2, CuO / 2 h / Heating
7: 70 percent / Pd23*CHCl3, P(o-tol)3 / toluene / 0.67 h / 80 °C
With
1H-imidazole; N-Bromosuccinimide; n-butyllithium; perchloric acid; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tris-(o-tolyl)phosphine; copper(II) oxide; copper dichloride;
In
dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)85633-7