Multi-step reaction with 11 steps
1.1: bromine / chloroform / Reflux
1.2: 20 °C
2.1: N-Bromosuccinimide / dibenzoyl peroxide / tetrachloromethane / Reflux
3.1: N,N-dimethyl-formamide / 80 °C
4.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 20 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
5.2: 5 h
6.1: tetrahydrofuran / 0.5 h / 0 - 20 °C
7.1: triethylamine / dichloromethane / 0.5 h / 20 °C
8.1: sodium azide / N,N-dimethyl-formamide / 20 °C
9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 100 °C
10.1: water; trimethylphosphane / tetrahydrofuran / 1 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / ethanol / Reflux; Inert atmosphere
With
N-Bromosuccinimide; sodium azide; oxalyl dichloride; water; bromine; sodium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trimethylphosphane;
tetrakis(triphenylphosphine) palladium(0); dibenzoyl peroxide;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;