Multi-step reaction with 9 steps
1.1: benzene / 6 h / 20 °C
2.1: SiO2 / CH2Cl2 / 24 h / 20 °C
3.1: 97 percent / N-bromosuccinimide; iP2NH / CH2Cl2 / 12 h / 20 °C
4.1: 94 percent / Cs2CO3 / acetone; dimethylformamide / 12 h / Heating
5.1: 98 percent / Na2S2O4; nBu4NBr; KOH / H2O; tetrahydrofuran / 4 h / 20 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: 72 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C
7.1: 90 percent / AgO; HNO3 / dioxane / 0.5 h / 20 °C
8.1: 97 percent / 2-iodoxybenzoic acid / dimethylsulfoxide; CH2Cl2 / 5 h / 20 °C
9.1: 86 percent / H2SO4; acetic acid / 0.17 h / 60 °C
With
silver(II) oxide; potassium hydroxide; N-Bromosuccinimide; n-butyllithium; sodium dithionite; sulfuric acid; tetrabutylammomium bromide; nitric acid; silica gel; caesium carbonate; acetic acid; diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1002/anie.200601992