Multi-step reaction with 13 steps
1: sulfuric acid / 5 h / 80 °C
2: bromine; acetic acid; sodium acetate / 12 h / 20 °C
3: N-chloro-succinimide / chloroform / 17 h / 60 °C
4: potassium carbonate / N,N-dimethyl acetamide / 24 h / 80 °C
5: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 20 °C
6: thionyl chloride / toluene / 22 h / Reflux
7: pyridine / dichloromethane / 21 h / 20 °C
8: tetrahydrofuran / 4 h / 20 °C
9: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; N,N-dimethyl-formamide / 18 h / 20 °C
10: n-butyllithium / tetrahydrofuran; hexane / -18 °C
11: triethylsilane; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile / 1 h / -78 °C
12: dmap / dichloromethane / 12 h / 20 °C
13: sodium ethanolate / N,N-dimethyl-formamide / 18 h / 20 °C
With
pyridine; triethylsilane; dmap; N-chloro-succinimide; n-butyllithium; thionyl chloride; lithium hydroxide monohydrate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; boron trifluoride diethyl etherate; bromine; sodium ethanolate; sodium acetate; potassium carbonate; acetic acid;
In
tetrahydrofuran; hexane; dichloromethane; chloroform; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; toluene; acetonitrile;