1.1: 99 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 2.1: 93 percent / thionyl chloride / CHCl3 / 0 - 20 °C 3.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 3.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 4.1: potassium hydroxide / H2O / 5 h / Heating 4.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 5.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 6.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 7.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 8.1: ozone / methanol; CH2Cl2 / -78 °C 8.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 9.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 10.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 10.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 10.3: 75 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating 11.1: 78 percent / sodium azide; boron trifluoride diethyl etherate; trifluoroacetic acid / CH2Cl2 / 0.25 h / 20 °C 12.1: 57 percent / 1,3,5-trimethyl-benzene / 6 h / Heating View Scheme

1: 1,4-dibromo-2,5-dimethylbenzene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.166667 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78 - 20°C; Further stages.;

n-butyllithium; isopropylmagnesium chloride in tetrahydrofuran; N,N-dimethyl-formamide

2-Nitropropane; sodium ethanolate in ethanol 30 h;

1: With phosphoric acid; hydrogen bromide; acetic acid 30 h; Heating; 2: With 2-Nitropropane; sodium ethanolate in ethanol 70 h; Further stages.;

1: 42 percent / 85percent phosphoric acid, 47percent hydrobromic acid / acetic acid / 1 h / Heating 2: 51 percent / 2-nitropropane, sodium ethoxide / ethanol / 30 h View Scheme

ethanol; 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane

diethyl ether

1: iodine; bromine 2: hexamethylenetetramine; ethanol View Scheme

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