Multi-step reaction with 10 steps
1: 24 percent / C3H7COONa / 150 °C
2: H2 / 10percent Pd/C / methanol / 2280 Torr
3: Br2, AcOH / 2.5 h / Ambient temperature
4: 30.0 g / polyphosphoric acid / 2.5 h / 100 °C
5: H2, AcONa / Pd/C
6: 1.) NaH / 1.) toluene, 0 deg C, 1 h, 2.) toluene, reflux, 4 h
7: 85 percent / conc. H2SO4 / CHCl3 / 0.67 h / Heating
8: 62 percent / NaOMe / methanol / 2.67 h / Heating
9: 1.) Et3N, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 2.) aq. NH4OH / 1.) CH3CN, RT, 45 min, 2.) CH3CN, RT, 30 min
10: 72 percent / BBr3 / CH2Cl2
With
ammonium hydroxide; PPA; C3H7COONa; sulfuric acid; hydrogen; bromine; sodium methylate; sodium acetate; boron tribromide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine;
palladium on activated charcoal;
In
methanol; dichloromethane; chloroform;
DOI:10.1021/jm960395q