Multi-step reaction with 8 steps
1: 1.) n-BuLi, TMEDA, 2.) triisopropyl borate, 3.) tetrakis(triphenylphosphine)palladium, Na2CO3
2: 100 percent / Br2 / CCl4 / 0.67 h / 0 - 5 °C
3: 92 percent / aq. NaOH / methanol / 3 h / Heating
4: 94 percent / toluene / 1 h / 80 °C
5: 70 percent / NBS / CCl4 / 3 h / Heating
6: 30 percent / K2CO3 / dimethylformamide / 40 h / Ambient temperature
7: 59 percent / aq. NaOH / methanol / 3 h / Heating
8: 1.) CDI / 1.) CH2Cl2, RT, 1 h, 2.) CH2Cl2, a) RT, 20 h, b) reflux, 4 h
With
sodium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; bromine; sodium carbonate; potassium carbonate; 1,1'-carbonyldiimidazole;
In
methanol; tetrachloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00045a016