Multi-step reaction with 12 steps
1: bromine / methanol; chloroform / 2 h
2: N,N-dimethyl-formamide / 16 h / 150 °C
3: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
4: lithium hydroxide monohydrate; water / tetrahydrofuran / 1 h / 20 °C
5: thionyl chloride / N,N-dimethyl-formamide / toluene / 16 h / 60 °C
6: triethylamine / chloroform / 2 h / 20 °C
7: 3-chloro-benzenecarboperoxoic acid / chloroform / 20 h / 20 °C
8: lithium chloride / N,N-dimethyl-formamide / 12 h / 130 °C
9: N-iodo-succinimide; trifluorormethanesulfonic acid / methanol; dichloromethane / 15 h / 20 °C
10: zinc / [2,2]bipyridinyl; nickel dibromide / N,N-dimethyl-formamide / 1 h / 80 °C
11: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
12: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 18 h / 20 °C
With
N-iodo-succinimide; thionyl chloride; lithium hydroxide monohydrate; trifluorormethanesulfonic acid; water; bromine; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; zinc;
[2,2]bipyridinyl; N,N-dimethyl-formamide; nickel dibromide;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;