2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene 14 h; Heating;

N,N'-bis(carboxymethyl)-ethylenediamine in tetrahydrofuran 8 h; Inert atmosphereReflux;

1: 92 percent / BF3*Et2O / dioxane / Heating 2: H2O, alkali 3: 94 percent / Cu(OAc)2 / propan-2-ol 4: 91 percent / PPE 5: EtSNa / dimethylformamide 6: DDQ / 1,2-dichloro-benzene View Scheme

1: 92 percent / BF3*Et2O / dioxane / Heating 2: H2O, alkali 3: 94 percent / Cu(OAc)2 / propan-2-ol 4: 91 percent / PPE 5: EtSNa / dimethylformamide 6: DDQ / 1,2-dichloro-benzene View Scheme

1: 94 percent / Cu(OAc)2 / propan-2-ol 2: 91 percent / PPE 3: EtSNa / dimethylformamide 4: DDQ / 1,2-dichloro-benzene View Scheme

1: H2O, alkali 2: 94 percent / Cu(OAc)2 / propan-2-ol 3: 91 percent / PPE 4: EtSNa / dimethylformamide 5: DDQ / 1,2-dichloro-benzene View Scheme

1: EtSNa / dimethylformamide 2: DDQ / 1,2-dichloro-benzene View Scheme

1: 91 percent / PPE 2: EtSNa / dimethylformamide 3: DDQ / 1,2-dichloro-benzene View Scheme

1: 1.) sodium methoxide 2: 71 percent / sodium isopropoxide / propan-2-ol / 24 h / Heating 3: 55 percent / 1,2-dichloro-benzene / 2 h / Heating 4: phosphoryl chloride / 5 h / 120 - 125 °C 5: 48 percent / potassium carbonate / dimethylformamide / 30 h / Ambient temperature 6: 70 percent / hydrogen chloride (gas) / 3 h / Heating 8: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / toluene / 14 h / Heating View Scheme

1: 73 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 36 h / Heating 2: 42 percent / dimethylformamide / Ambient temperature 3: 48 percent / K2CO3 / dimethylformamide / 30 h 4: 70 percent / HCl / 1 h / Heating 6: 52 percent / 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) / toluene / 14 h / Heating View Scheme