Multi-step reaction with 13 steps
1.1: HCl / 1,1,2,2-tetrachloro-ethane / 1 h / 17 °C
1.2: 61 percent / AlCl3 / 1,1,2,2-tetrachloro-ethane / 3 h / 55 °C
2.1: 92 percent / NaOH / ethanol / 20 °C
3.1: Br2 / CH2Cl2 / 20 °C
4.1: AcOH
5.1: 73 percent / DBU / tetrahydrofuran / 55 °C
6.1: 75 percent / 17 h / 190 °C
7.1: 48 g / AIBN; NBS / CCl4 / 2 h / Heating
8.1: dimethylformamide / 5 h / 100 °C
9.1: 68.5 percent / aq. NaOH / CH2Cl2 / 3 h / 35 - 40 °C
10.1: CuBr / tetrahydrofuran
10.2: 100 percent / aq. H2SO4 / tetrahydrofuran
11.1: 100 percent / aq. HBr; AcOH / 3 h / Heating
12.1: 26.5 percent / NaOH; TMU; Aliquat / 11 h / 50 °C
13.1: tetrahydrofuran / 20 °C
With
hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); Aliquat; hydrogen bromide; bromine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; tetramethylurea; copper(I) bromide;
In
tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; 1,1,2,2-tetrachloroethane;
9.1: Wittig reaction;
DOI:10.1021/jm020536q