Multi-step reaction with 11 steps
1.1: bromine; acetic acid / 23.5 h
2.1: potassium carbonate / acetonitrile / 0.5 h / 80 °C / Inert atmosphere
3.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 0.5 h / 120 °C / Inert atmosphere; Microwave
4.1: 1,2-dimethoxyethane; water / 0.5 h / 120 °C
5.1: Hoveyda-Grubbs catalyst / dichloromethane / 48 h / 20 °C
6.1: hydrogen / 5% rhodium-on-charcoal / ethyl acetate / 5 h / 1875.19 Torr
7.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3.5 h / Inert atmosphere
8.1: boron tribromide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
8.2: 0 °C
9.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 4 h / 100 °C / Inert atmosphere
10.1: water; lithium hydroxide / tetrahydrofuran; methanol / 24 h / 20 °C
11.1: copper(I) oxide / 1-methyl-pyrrolidin-2-one / 0.25 h / 190 °C / Inert atmosphere; Sealed vial
With
copper(I) oxide; N-Bromosuccinimide; water; hydrogen; bromine; boron tribromide; potassium carbonate; acetic acid; lithium hydroxide;
tetrakis(triphenylphosphine) palladium(0); 5% rhodium-on-charcoal;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;