Multi-step reaction with 11 steps
1: 91 percent / K2CO3, tetrakis(triphenylphosphine)palladium(0) / toluene; methanol; H2O / 24 h / 80 °C
2: 60 percent / HBr, AcOH / 24 h / 118 °C
3: 81 percent / HCl / Ambient temperature
4: 98.7 percent / pyridine / CH2Cl2 / 2 h / Ambient temperature
5: 78 percent / LiCl, PdCl2(Ph3P)2 / dimethylformamide / 12 h / Ambient temperature
6: DIBAL-H / CH2Cl2 / 4 h / Ambient temperature
7: imidazole / dimethylformamide / 12 h / Ambient temperature
8: 1.) 9-BBN, 2.) 1 N aq. NaOH, 30percent H2O2 / 1.) THF, RT, 12 h, 2.) THF, 30 min
9: CrO3, H2SO4 / acetone / 0 °C
10: CH2Cl2 / 1 h / Ambient temperature
11: CH2Cl2 / 24 h / Ambient temperature
With
pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium(0); sulfuric acid; hydrogen bromide; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; acetic acid; lithium chloride;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jm9506985