boron trichloride in dichloromethane T=-70 - -65°C; 1 h;

1: KOH / ethanol / Heating 2: K2CO3 / dimethylformamide / 120 °C 3: 1.) thallium(III) nitrate (TTN), 2.) NaHSO3 / 1.) MeOH, 60 deg C, 2.) 0 deg C, 30 min 4: 1.) H2, 2.) 10percent HCl / 10percent Pd/C / 1.) MeOH, 2.) MeOH, reflux 5: aq. NaBH4 / tetrahydrofuran / 0.5 h / 0 °C 6: TsOH*H2O / toluene / 110 °C 7: BCl3 / CH2Cl2 / 1 h / -70 - -65 °C View Scheme

1: K2CO3 / dimethylformamide / 120 °C 2: 1.) thallium(III) nitrate (TTN), 2.) NaHSO3 / 1.) MeOH, 60 deg C, 2.) 0 deg C, 30 min 3: 1.) H2, 2.) 10percent HCl / 10percent Pd/C / 1.) MeOH, 2.) MeOH, reflux 4: aq. NaBH4 / tetrahydrofuran / 0.5 h / 0 °C 5: TsOH*H2O / toluene / 110 °C 6: BCl3 / CH2Cl2 / 1 h / -70 - -65 °C View Scheme

1: 1.) thallium(III) nitrate (TTN), 2.) NaHSO3 / 1.) MeOH, 60 deg C, 2.) 0 deg C, 30 min 2: 1.) H2, 2.) 10percent HCl / 10percent Pd/C / 1.) MeOH, 2.) MeOH, reflux 3: aq. NaBH4 / tetrahydrofuran / 0.5 h / 0 °C 4: TsOH*H2O / toluene / 110 °C 5: BCl3 / CH2Cl2 / 1 h / -70 - -65 °C View Scheme

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 30 h; Heating;

1: 75 mg / 48percent HBr / 6 h / Heating 2: 35 mg / DDQ / benzene / 30 h / Heating View Scheme

1: 320 mg / Heating 2: 75 mg / 48percent HBr / 6 h / Heating 3: 35 mg / DDQ / benzene / 30 h / Heating View Scheme

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

1: TsOH*H2O / toluene / 110 °C 2: BCl3 / CH2Cl2 / 1 h / -70 - -65 °C View Scheme

1: aq. NaBH4 / tetrahydrofuran / 0.5 h / 0 °C 2: TsOH*H2O / toluene / 110 °C 3: BCl3 / CH2Cl2 / 1 h / -70 - -65 °C View Scheme