Multi-step reaction with 11 steps
1.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 - 20 °C
1.2: 0 - 20 °C
2.1: 2-methyl-but-2-ene; water; sodium chlorite; sodium dihydrogenphosphate / tert-butyl alcohol / 0.5 h / 20 °C
2.2: pH 1
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
4.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C
5.1: N-chloro-succinimide / acetonitrile / 45 h / 60 °C
6.1: boron tribromide / dichloromethane / 0.75 h / -78 - 0 °C
6.2: 0.17 h / 20 °C
7.1: potassium carbonate / acetone / 20 °C
8.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.17 h / -78 - 0 °C / Inert atmosphere
8.2: 0.5 h / 20 °C
9.1: sodium tetrahydroborate; methanol
10.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; chlorobenzene; methanol / 5 h
11.1: sodium acetate; bromine; acetic acid / 0.22 h
11.2: 50 °C
With
methanol; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-chloro-succinimide; 2-methyl-but-2-ene; oxalyl dichloride; water; hydrogen; bromine; isopropylmagnesium chloride; sodium acetate; boron tribromide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; lithium chloride;
palladium 10% on activated carbon; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; chlorobenzene; acetone; toluene; acetonitrile; tert-butyl alcohol;