1: With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene T=-78°C; 0.333333 h; 2: With iodine in tetrahydrofuran; n-heptane; ethylbenzene T=-78°C; 5 h;

iodine; sodium thiosulfate; lithium diisopropyl amide in tetrahydrofuran; n-heptane; dichloromethane; chloroform; ethylbenzene; water

1.1: 2.47 g / aq. NaOH / ethanol / 1 h / Heating 2.1: thionyl chloride / 2 h / Heating 3.1: 10.9 g / aq. ammonia / acetone / 10 °C 4.1: 9.0 g / cyanuric chloride / dimethylformamide / 0.5 h 5.1: LDA / heptane; tetrahydrofuran; ethylbenzene / 0.33 h / -78 °C 5.2: 750 mg / iodine / heptane; tetrahydrofuran; ethylbenzene / 5 h / -78 °C View Scheme

1.1: thionyl chloride / 2 h / Heating 2.1: 10.9 g / aq. ammonia / acetone / 10 °C 3.1: 9.0 g / cyanuric chloride / dimethylformamide / 0.5 h 4.1: LDA / heptane; tetrahydrofuran; ethylbenzene / 0.33 h / -78 °C 4.2: 750 mg / iodine / heptane; tetrahydrofuran; ethylbenzene / 5 h / -78 °C View Scheme

1.1: 9.0 g / cyanuric chloride / dimethylformamide / 0.5 h 2.1: LDA / heptane; tetrahydrofuran; ethylbenzene / 0.33 h / -78 °C 2.2: 750 mg / iodine / heptane; tetrahydrofuran; ethylbenzene / 5 h / -78 °C View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate in ethylene glycol dimethyl ether 4 h; Heating;