Multi-step reaction with 9 steps
1: 100 percent / Py / CH2Cl2 / 20 °C
2: HBr / CHCl3
3: 1.) Hg(CN)2, HgBr2, molecular sieves 4 Angstroem / 1.) CH3CN, 20 deg C, 45 min, 2.) CH3CN, 1 h
4: 91 percent / MeONa, MeOH / CH2Cl2 / 20 h / 20 °C
5: 1.) Bu2SnO, 2.) tetrabutylammonium bromide / 1.) toluene, reflux, 2.) toluene, 55 deg C, 36 h
6: pyridine / CH2Cl2 / 20 h / 20 °C
7: aq. cerium(IV) ammonium nitrate / acetonitrile / 0.33 h / 20 °C
8: BF3*Et2O / CH2Cl2 / 0.5 h / 0 °C
9: H2 / 10percent Pd/C / ethyl acetate; ethanol / 2 h / 40 - 42 °C
With
pyridine; methanol; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; hydrogen bromide; hydrogen; sodium methylate; mercury(II) cyanide; di(n-butyl)tin oxide; mercury dibromide;
palladium on activated charcoal;
In
ethanol; dichloromethane; chloroform; ethyl acetate; acetonitrile;