sulfuric acid; nitric acid T=10°C; 1.5 h;

boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) CH2Cl2, room temp., 15 h, 2.) CH2Cl2, room temp., 2 h; Yield given. Multistep reaction. Yields of byproduct given;

boron trifluoride diethyl etherate; chloranil 1.) CH2Cl2, 20 h, 2.) reflux, 4 h; Yield given. Multistep reaction. Yields of byproduct given;

hydrogenchloride; tin(ll) chloride T=50 - 60°C; Versetzen der Reaktionsloesung mit wss. NaNO2-Loesung und anschliessendes Kochen mit CuCl in wss. HCl;

potassium hydroxide T=100°C;

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sodium tetrahydroborate in methanol T=10°C; 1 h;

1: 71 percent / sodium acetate, NaBH3CN / methanol / 0.75 h / Ambient temperature 2: 1.) BH3*THF, 2.) NaOAc / 1.) glyme, RT, 72 h, 2.) n-BuOH, reflux, 72 h 3: 1.93 g / Na2CO3, KI / dimethylformamide / 16 h / Ambient temperature 4: 1.75 g / LAH / tetrahydrofuran / 8 h / Heating 5: 54 percent / tetrahydrofuran / 0.5 h / Heating View Scheme

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