Multi-step reaction with 8 steps
1.1: 70 percent / I2; HIO3; aq. H2SO4 / acetic acid; CCl4 / 30 h / 65 °C
2.1: tert-butyllithium / tetrahydrofuran; diethyl ether; pentane / 5 h / -78 - 0 °C
2.2: 95 percent / tetrahydrofuran; diethyl ether; pentane / 24 h / 20 °C
3.1: sec-butyllithium; TMEDA / diethyl ether; pentane / 0.17 h / -78 °C
3.2: I2 / diethyl ether; pentane / 24 h / 20 °C
3.3: 65 percent / NaHSO3 / H2O; diethyl ether; pentane
4.1: 60 percent / P(o-Tolyl)3; Et3N; Pd(OAc)2 / dimethylformamide / 1 h / 80 °C
5.1: 90 percent / P(o-Tolyl)3; Et3N; Pd(OAc)2 / dimethylformamide / 80 °C
6.1: 100 percent / H2 / 10percent Pd/C / methanol / 16 h / 20 °C / 2585.81 Torr
7.1: 70 percent / DPPA; Et3N / 24 h / Heating
8.1: K2CO3; ICl / CCl4 / 1 h / 0 °C
8.2: 95 percent / NaHSO3 / H2O; CCl4 / 1 h / 20 °C
With
palladium diacetate; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; diphenyl-phosphinic acid; hydrogen; iodine; tert.-butyl lithium; sec.-butyllithium; Iodine monochloride; iodic acid; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine;
10percent Pd/C;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; acetic acid; N,N-dimethyl-formamide; pentane;
4.1: Heck reaction / 5.1: Heck reaction / 7.1: Curtius rearangement;
DOI:10.1021/ja020675x