Multi-step reaction with 10 steps
1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / ethyl acetate / 0.33 h / Reflux
2.1: N,N-dimethyl-formamide / 3 h / 80 °C
3.1: potassium hydroxide; water / tetrahydrofuran; ethanol / 3 h / 80 °C
4.1: pyridinium p-toluenesulfonate / tetrahydrofuran / 2 h / 0 °C
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.42 h / -78 °C / Inert atmosphere
5.2: 0.08 h
6.1: toluene-4-sulfonic acid / tetrahydrofuran; methanol / 15 h / 20 °C
7.1: chloro-trimethyl-silane / dimethyl sulfoxide / 4 h / 20 °C
7.2: 1 h / 0 - 20 °C
8.1: tetrabutylammomium bromide; bis(cyclopentadienyl)titanium dichloride; sodium carbonate / water; N,N-dimethyl-formamide / 15 h / 85 °C
9.1: bis(dibenzylideneacetone)-palladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; potassium fluoride / tetrahydrofuran / 0.5 h / 100 °C / Microwave irradiation
10.1: potassium carbonate; methanol / 1.5 h / 20 °C
With
methanol; bis(cyclopentadienyl)titanium dichloride; potassium fluoride; N-Bromosuccinimide; n-butyllithium; chloro-trimethyl-silane; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; 2,2'-azobis(isobutyronitrile); tetrabutylammomium bromide; water; pyridinium p-toluenesulfonate; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; potassium hydroxide; bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; methanol; ethanol; hexane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm300884k