1: 46 percent / morpholine 2: 86 percent / BBr3 / CH2Cl2 3: 32 percent / DDQ / tetrahydrofuran 4: 43 percent / Pyr*HCl / Heating View Scheme

1: AlCl3 / 1,2-dichloro-ethane 2: 68 percent / AlCl3 / CHCl3 3: 46 percent / morpholine 4: 86 percent / BBr3 / CH2Cl2 5: 32 percent / DDQ / tetrahydrofuran 6: 43 percent / Pyr*HCl / Heating View Scheme

1: 86 percent / BBr3 / CH2Cl2 2: 32 percent / DDQ / tetrahydrofuran 3: 43 percent / Pyr*HCl / Heating View Scheme

1: 68 percent / AlCl3 / CHCl3 2: 46 percent / morpholine 3: 86 percent / BBr3 / CH2Cl2 4: 32 percent / DDQ / tetrahydrofuran 5: 43 percent / Pyr*HCl / Heating View Scheme

1: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 2: hydrogenchloride; water / methanol / 12 h / 50 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 0.75 h / 60 °C / Inert atmosphere View Scheme

1: hydrogenchloride; water / methanol / 12 h / 50 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 0.75 h / 60 °C / Inert atmosphere View Scheme

1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 2: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 3: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 4: hydrogenchloride; water / methanol / 12 h / 50 °C 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 0.75 h / 60 °C / Inert atmosphere View Scheme

1: iodine; silver(I) acetate / chloroform / 5 h / 20 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 3: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 4: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 5: hydrogenchloride; water / methanol / 12 h / 50 °C 6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 0.75 h / 60 °C / Inert atmosphere View Scheme

1.1: acetyl chloride; zinc dibromide / dichloromethane / 3 h / 20 °C / Inert atmosphere 1.2: 3 h / Inert atmosphere; Cooling with ice 2.1: iodine; silver(I) acetate / chloroform / 5 h / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 4.1: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 5.1: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 6.1: hydrogenchloride; water / methanol / 12 h / 50 °C 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 0.75 h / 60 °C / Inert atmosphere View Scheme