Multi-step reaction with 13 steps
1.1: magnesium chloride / tetrahydrofuran / 2.5 h / 10 - 50 °C / Industry scale
1.2: 18.5 h / 30 - 34 °C / Industry scale
2.1: sodium tetrahydroborate / 1.42 h / 10 - 39 °C
2.2: 0 - 5 °C
3.1: dmap / tetrahydrofuran / 3 h / 20 - 35 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 35 - 50 °C
5.1: hydrogen / palladium(II) hydroxide / ethanol / 5 h / 30 °C / 155.15 Torr
6.1: sodium hydroxide; water / ethanol / 16 h
6.2: 1 h / 0 - 5 °C / pH 1
7.1: thionyl chloride / N,N-dimethyl-formamide / chlorobenzene / 1.5 h / 21 °C
8.1: bromine / chlorobenzene / 20 h / 85 - 90 °C
9.1: water / chlorobenzene / 21 h / 0 - 5 °C
10.1: sulfurous dibromide / 16 h / 40 - 60 °C / Industry scale
11.1: caesium carbonate / butanone / 0.28 h / Industry scale
11.2: 13.8 h / 54 °C / Industry scale
12.1: sodium hydroxide; water / butanone / 1.72 h / 12 - 18 °C / Industry scale
12.2: 3 h / pH 3.2 / Industry scale
13.1: isopropyl alcohol; water / 20 - 70 °C / Industry scale
With
dmap; sodium tetrahydroborate; sulfurous dibromide; thionyl chloride; water; hydrogen; bromine; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide; magnesium chloride;
palladium(II) hydroxide; N,N-dimethyl-formamide;
In
tetrahydrofuran; ethanol; water; chlorobenzene; isopropyl alcohol; butanone;