(i) NaNO2, aq. HCl, (ii) /BRN= 4652394/, CuSO4, (iii) NO2/HNO3; Multistep reaction;

1: 98 percent / aq. NaNO2; glacial acetic acid / 0.33 h 2: 75 percent / NH4(+)HCOO(-); H2 / Pd/C / ethanol View Scheme

1.1: hydrogen bromide / 1,4-dioxane; water / 0.75 h / 60 °C / Inert atmosphere 1.2: 2.33 h / 0 - 8 °C / Inert atmosphere 1.3: 20.5 h / 20 - 60 °C / Inert atmosphere 2.1: hydrogenchloride; iron / ethanol; water / 21 h / 20 °C / Reflux; Inert atmosphere 3.1: sulfuric acid; sodium nitrite / water / 0.5 h / 0 - 10 °C / Inert atmosphere 3.2: 0.33 h / 0 °C / Inert atmosphere 3.3: 145 °C / Inert atmosphere View Scheme

acetic acid; sodium nitrite 0.333333 h;

acetic acid Diazotization;

1.1: N-chloro-succinimide / methanol / 4 h / 60 °C 2.1: sulfuric acid; acetic acid; sodium nitrite / 0.5 h / 23 °C 2.2: 23 °C 3.1: iron; ammonium chloride / ethanol; water / 0.5 h / Reflux 4.1: sulfuric acid; acetic acid; sodium nitrite / 0.5 h / 23 °C 4.2: Reflux View Scheme

1.1: N-chloro-succinimide / methanol / 4 h / 60 °C 2.1: sulfuric acid; acetic acid; sodium nitrite / 0.5 h / 23 °C 2.2: 23 °C 3.1: iron; ammonium chloride / ethanol; water / 0.5 h / Reflux View Scheme

1.1: N-chloro-succinimide / methanol / 4 h / 60 °C 2.1: sulfuric acid; acetic acid; sodium nitrite / 0.5 h / 23 °C 2.2: 23 °C 3.1: iron; ammonium chloride / ethanol; water / 0.5 h / Reflux 4.1: sulfuric acid; acetic acid; sodium nitrite / 0.5 h / 23 °C 4.2: Reflux 5.1: potassium carbonate / acetonitrile / 12 h / 23 °C 6.1: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; triethylamine / acetonitrile / 3 h / Reflux 7.1: boron tribromide / dichloromethane / 0.17 h / 0 °C 7.2: Cooling 8.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 0.67 h / 120 °C / Inert atmosphere; Microwave irradiation 9.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere 10.1: hydrogenchloride / 1,4-dioxane; methanol / 12 h / 23 °C 11.1: triethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 75 °C View Scheme

1: aq. HCl; SnCl2 2: 65 percent / thionyl chloride / benzene / 72 h 3: 86 percent / bromine; aq. HBr / 16 h / Heating View Scheme

1: 80 percent / NaNO2; AcOH 2: Cl2 / acetic acid / 5 h View Scheme