Multi-step reaction with 7 steps
1: 98 percent / K2CO3 / dimethylformamide / 15 h / Ambient temperature
2: 1.) Al(CH3)3 / 1.) toluene, 25 deg C, 1 h, 2.) toluene, 75 deg C, 18 h
3: 86 percent / various solvent(s) / 6 h / 210 °C
4: 88 percent / Br2, tert-BuNH2 / toluene; CH2Cl2 / 3 h / -60 - -5 °C
5: 96 percent / imidazole / dimethylformamide / 2 h / Ambient temperature
6: 82 percent / tetrahydrofuran; diethyl ether / 8 h / -70 °C
7: t-BuLi; TMEDA / 1.) THF, pentane, -90 deg C, 40 min, 2.) THF, -90 deg C to -30 deg C, 90 min
With
1H-imidazole; N,N,N,N,-tetramethylethylenediamine; bromine; trimethylaluminum; tert.-butyl lithium; potassium carbonate; tert-butylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00119a036