Multi-step reaction with 7 steps
1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1 h / 0 °C / Inert atmosphere
2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / diethyl ether; toluene; hexane / 0.33 h / -78 °C / Inert atmosphere
2.2: 1 h / 0 °C / Inert atmosphere; Cooling with ice
2.3: 1 h / 20 °C / Inert atmosphere
3.1: sodium periodate; periodic acid / tetrahydrofuran; water / 4 h / 0 - 20 °C / Inert atmosphere
4.1: diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
5.1: magnesium bromide ethyl etherate / diethyl ether / Inert atmosphere; Reflux
6.1: magnesium; iodine / tetrahydrofuran / 1 h / Inert atmosphere; Reflux
6.2: 1.33 h / -78 - 20 °C / Inert atmosphere
6.3: 0 °C / Inert atmosphere
7.1: ruphos; potassium phosphate; palladium diacetate / water; toluene / 12 h / 80 °C / Schlenk technique; Inert atmosphere
With
potassium phosphate; sodium periodate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodine; palladium diacetate; magnesium bromide ethyl etherate; magnesium; periodic acid; 3-chloro-benzenecarboperoxoic acid; ruphos;
In
tetrahydrofuran; diethyl ether; hexane; chloroform; water; toluene;
4.1: |Grignard Reaction / 7.1: |Suzuki Coupling;
DOI:10.1016/j.tet.2016.03.041