Multi-step reaction with 9 steps
1.1: acetic acid / 0.75 h / 0 - 20 °C
1.2: 0 - 20 °C
2.1: sodium nitrite; phosphoric acid / water / 0.33 h / 0 °C
2.2: 20 °C / Cooling with ice
3.1: boron tribromide / dichloromethane / 2 h / 0 °C
4.1: bromine; acetic acid / 1 h / 20 °C
5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 0.17 h / 110 °C / Microwave irradiation
6.1: pyridine / dichloromethane / 1 h / 0 °C
7.1: lithium chloride / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.5 h / 120 °C / Microwave irradiation
8.1: sodium sulfite; AD-mix α / water; tert-butyl alcohol / 0 - 20 °C
9.1: pyridine / dichloromethane / 20 °C
With
pyridine; AD-mix α; phosphoric acid; bromine; boron tribromide; potassium carbonate; acetic acid; lithium chloride; sodium sulfite; sodium nitrite;
bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium(0);
In
1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;