Multi-step reaction with 10 steps
1.1: acetic acid / tetrahydrofuran; diethyl ether / 3.5 h / -12 - -10 °C
2.1: boron tribromide / toluene / 3 h / -25 - -5 °C
2.2: 0.5 h / 7 °C
3.1: thionyl chloride / 35.5 h / -10 °C
4.1: potassium carbonate; dmap / dimethyl sulfoxide / 87 h / 60 °C
5.1: potassium hydroxide / 1-methyl-pyrrolidin-2-one / 0.42 h / 120 °C
6.1: N,N-dimethyl-formamide; thionyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C
6.2: 0.5 h / 0 - 5 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; N-Bromosuccinimide / methanol / 22 h / -10 - -5 °C
8.1: potassium hydroxide / 1-methyl-pyrrolidin-2-one / 2 h / 110 - 120 °C
9.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 35 °C
10.1: palladium 10% on activated carbon / tetrahydrofuran; water / 88 h / 10343.2 - 46544.6 Torr
With
dmap; N-Bromosuccinimide; thionyl chloride; palladium 10% on activated carbon; boron tribromide; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; potassium hydroxide;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; water; dimethyl sulfoxide; toluene;