potassium carbonate; xylene

potassium carbonate in N,N-dimethyl-formamide T=20 - 60°C; 3 h;

1.1: potassium carbonate / dimethylformamide / 6 h / 80 °C 2.1: H2 / Pd/C / methanol / 27 h / 20 °C 3.1: aq. HBr; NaNO2 / 0 - 5 °C 3.2: CuBr; aq. HBr / 60 °C 4.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C 4.2: tetrahydrofuran; hexane / -78 - 20 °C 5.1: oxalyl chloride; DMF / CH2Cl2 / 20 °C 6.1: n-BuLi / hexane; tetrahydrofuran / -78 °C 6.2: 4.70 g / hexane; tetrahydrofuran; CH2Cl2 / -78 - 10 °C View Scheme

1.1: potassium carbonate / dimethylformamide / 6 h / 80 °C 2.1: H2 / Pd/C / methanol / 27 h / 20 °C 3.1: aq. HBr; NaNO2 / 0 - 5 °C 3.2: CuBr; aq. HBr / 60 °C View Scheme

2: 94 percent / hydrogen / 5percent Pd/C / ethyl acetate / 24 h View Scheme

1: With water; tin(ll) chloride in tetrahydrofuran T=80°C; 2 h; 2: With sodium hydrogencarbonate in water

1.1: potassium carbonate / dimethylformamide / 6 h / 80 °C 2.1: H2 / Pd/C / methanol / 27 h / 20 °C 3.1: aq. HBr; NaNO2 / 0 - 5 °C 3.2: CuBr; aq. HBr / 60 °C 4.1: LDA / tetrahydrofuran; hexane / 1.5 h / -78 °C 4.2: tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: potassium carbonate / acetone / 3 h / 65 °C 2.1: acetic acid; iron / 20 °C 2.2: pH 7 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C View Scheme

triphenylphosphine; diethylazodicarboxylate in dichloromethane T=20°C; 20 h;

1.1: potassium carbonate / acetone / 3 h / 65 °C 2.1: acetic acid; iron / 20 °C 2.2: pH 7 View Scheme