Multi-step reaction with 6 steps
1: 86 percent / Br2, I2 / 2 h / 23 °C
2: 1.) Li / 1.) ether, reflux, 4 h, 2.) ether, 23 deg C, 30 min
3: 1.) TMEDA / 1.) THF, -78 deg C, 45 min, 2.) THF, from -78 deg C to 23 deg c, 2 h
4: PDC, celite / dimethylformamide / 12 h / 23 °C
5: HOBT, Et3N, EDC / dimethylformamide / 12 h / 0 - 25 °C
6: 1.) s-BuLi, TMEDA / 1.) THF, -78 deg C, 45 min, 2.) THF, from -78 deg C to 23 deg c, 2 h
With
dipyridinium dichromate; N,N,N,N,-tetramethylethylenediamine; Celite; bromine; iodine; sec.-butyllithium; lithium; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine;
In
N,N-dimethyl-formamide;
DOI:10.1021/jm960093o