1.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 1.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 1.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 2.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 3.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: n-butyl lithium / hexane; tetrahydrofuran / 0.17 h / -78 °C 1.2: 99 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: 99 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 3.1: 93 percent / thionyl chloride / CHCl3 / 0 - 20 °C 4.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 4.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 5.1: potassium hydroxide / H2O / 5 h / Heating 5.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 6.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 7.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 8.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 9.1: ozone / methanol; CH2Cl2 / -78 °C 9.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 10.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 11.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 11.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 11.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 12.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 13.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

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 / 1.2 h / -20 - -10 °C 10.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 10.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 11.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 12.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: 93 percent / thionyl chloride / CHCl3 / 0 - 20 °C 2.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 2.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 3.1: potassium hydroxide / H2O / 5 h / Heating 3.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 4.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 5.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 6.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 7.1: ozone / methanol; CH2Cl2 / -78 °C 7.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 8.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 9.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 9.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 9.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 10.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 11.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: sodium hydride / 1,2-dimethoxy-ethane; various solvent(s) / 2 h / 20 °C 1.2: 88 percent / 1,2-dimethoxy-ethane; various solvent(s) / 12 h / Heating 2.1: potassium hydroxide / H2O / 5 h / Heating 2.2: 83 percent / sulfuric acid / H2O / 20 h / Heating 3.1: 88 percent / polyphosphoric acid / 2.5 h / 100 °C 4.1: 98 percent / sodium borohydride / ethanol / 1 h / 0 - 20 °C 5.1: 86 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 6.1: ozone / methanol; CH2Cl2 / -78 °C 6.2: dimethyl sulfide; sodium hydrogen carbonate / methanol; CH2Cl2 / 4 h / 20 °C 7.1: 101 mg / aq. NH3 / CH2Cl2; methanol / 12 h / 20 °C 8.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 8.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 8.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 9.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 10.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: conc. HCl; sodium nitrite / H2O / 0.5 h / 0 °C 1.2: potassium carbonate / H2O; acetonitrile / 0 - 20 °C 2.1: i-PrMgCl*LiCl / tetrahydrofuran / 1.2 h / -20 - -10 °C 2.2: ZnBr2 / tetrahydrofuran / 0.5 h / -10 - -5 °C 2.3: 63 percent / Pd(PPh3)4 / tetrahydrofuran / 5 h / Heating 3.1: 94 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C 4.1: 68 percent / 1,3,5-trimethyl-benzene / 5 h / Heating View Scheme

1.1: toluene-4-sulfonic acid / ethanol / 1.5 h / Reflux 2.1: trichlorophosphate / 1,2-dichloro-benzene / 1.5 h / 20 °C 2.2: 4 h / 105 °C 2.3: 20 °C 3.1: 3 h / 115 °C / Inert atmosphere 3.2: 1 h / 20 °C / Molecular sieve; Inert atmosphere 4.1: sodium carbonate; p-toluenesulfonyl chloride / tetrahydrofuran; water / 2 h / 20 °C 4.2: 12 h 4.3: 0 °C / pH 10 View Scheme

1.1: trichlorophosphate / 1,2-dichloro-benzene / 1.5 h / 20 °C 1.2: 4 h / 105 °C 1.3: 20 °C 2.1: 3 h / 115 °C / Inert atmosphere 2.2: 1 h / 20 °C / Molecular sieve; Inert atmosphere 3.1: sodium carbonate; p-toluenesulfonyl chloride / tetrahydrofuran; water / 2 h / 20 °C 3.2: 12 h 3.3: 0 °C / pH 10 View Scheme

1.1: 3 h / 115 °C / Inert atmosphere 1.2: 1 h / 20 °C / Molecular sieve; Inert atmosphere 2.1: sodium carbonate; p-toluenesulfonyl chloride / tetrahydrofuran; water / 2 h / 20 °C 2.2: 12 h 2.3: 0 °C / pH 10 View Scheme

acetic acid 1.) tetrahydrofuran, -78 deg C, 0.5 h, 2.) reflux, 1 h; Yield given. Multistep reaction;