1,2-Dibromo-4,5-diiodobenzene

Conditions: temp:82.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 200 ml Schlenk reaction vessel were added under a nitrogen atmosphere 3.074 g (6.30 mmol) of 1,2-dibromo-4,5-diiodobenzene synthesized in Synthetic Example 3, 600 mg (0.519 mmol) of tetrakis(triphenylphosphine)palladium (manufactured by Tokyo Chemical Industry Co. Ltd.), and 1.920 mg (15.7 mmol) of phenylboronic acid (manufactured by Wako Pure Chemical Industries, Ltd.). Further, 50 ml of toluene, 13 ml of ethanol, and an aqueous solution composed of 4.007 g (37.8 mol) of sodium carbonate and 16 ml of water were added. The whole was heated to 82° C. and stirred for 24 hours. After cooling to room temperature, toluene and water were added and phase separation was conducted. The organic phase was concentrated and the resulting residue was dissolved in 26 ml of toluene. Then, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto, followed by 2 hours of stirring at room temperature. The toluene solution was washed twice with water and then the organic phase was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: hexane) to obtain a white solid of 1,2-dibromo-4,5-diphenylbenzene (1.953 g, yield 80%). were added After cooling to room temperature phase separation The organic phase was concentrated the resulting residue was dissolved in 26 ml of toluene Then, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added followed by 2 hours of stirring at room temperature The toluene solution was washed twice with water the organic phase was concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (solvent: hexane)

Conditions: temp:82.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 200 ml Schlenk reaction vessel were added under a nitrogen atmosphere 3.074 g (6.30 mmol) of 1,2-dibromo-4,5-diiodobenzene synthesized in Synthetic Example 3, 600 mg (0.519 mmol) of tetrakis(triphenylphosphine)palladium (manufactured by Tokyo Chemical Industry Co. Ltd.), and 1.920 mg (15.7 mmol) of phenylboronic acid (manufactured by Wako Pure Chemical Industries, Ltd.). Further, 50 ml of toluene, 13 ml of ethanol, and an aqueous solution composed of 4.007 g (37.8 mol) of sodium carbonate and 16 ml of water were added. The whole was heated to 82° C. and stirred for 24 hours. After cooling to room temperature, toluene and water were added and phase separation was conducted. The organic phase was concentrated and the resulting residue was dissolved in 26 ml of toluene. Then, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto, followed by 2 hours of stirring at room temperature. The toluene solution was washed twice with water and then the organic phase was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: hexane) to obtain a white solid of 1,2-dibromo-4,5-diphenylbenzene (1.953 g, yield 80%). were added After cooling to room temperature phase separation The organic phase was concentrated the resulting residue was dissolved in 26 ml of toluene Then, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added followed by 2 hours of stirring at room temperature The toluene solution was washed twice with water the organic phase was concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (solvent: hexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1 L three-necked flask fitted with a mechanical stirrer were added 36.9 g (162 mmol) of periodic acid and 150 ml of sulfuric acid. After periodic acid was dissolved, 80.7 g (486 mmol) of potassium iodide was added portionwise. The temperature of the content was cooled to 0° C. and 75.0 g (318 mmol) of 1,2-dibromobenzene was added. The resulting mixture was stirred at 0° C. for 30 minutes. After the reaction mixture was poured into ice, the whole was filtrated and a solid was taken out. The solid was recrystallized from THF/methanol twice to obtain white crystals of 1,2-dibromo-4,5-diiodobenzene (76.2 g, yield 49%). To a 1 L three-necked flask fitted with a mechanical stirrer After the reaction mixture was poured into ice the whole was filtrated The solid was recrystallized from THF/methanol twice

Conditions: temp:82.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 200 ml Schlenk reaction vessel were added under a nitrogen atmosphere 3.074 g (6.30 mmol) of 1,2-dibromo-4,5-diiodobenzene synthesized in Synthetic Example 3, 600 mg (0.519 mmol) of tetrakis(triphenylphosphine)palladium (manufactured by Tokyo Chemical Industry Co. Ltd.), and 1.920 mg (15.7 mmol) of phenylboronic acid (manufactured by Wako Pure Chemical Industries, Ltd.). Further, 50 ml of toluene, 13 ml of ethanol, and an aqueous solution composed of 4.007 g (37.8 mol) of sodium carbonate and 16 ml of water were added. The whole was heated to 82° C. and stirred for 24 hours. After cooling to room temperature, toluene and water were added and phase separation was conducted. The organic phase was concentrated and the resulting residue was dissolved in 26 ml of toluene. Then, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto, followed by 2 hours of stirring at room temperature. The toluene solution was washed twice with water and then the organic phase was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent: hexane) to obtain a white solid of 1,2-dibromo-4,5-diphenylbenzene (1.953 g, yield 80%). were added After cooling to room temperature phase separation The organic phase was concentrated the resulting residue was dissolved in 26 ml of toluene Then, 1.0 ml of a 70% tert-butyl hydroperoxide solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added followed by 2 hours of stirring at room temperature The toluene solution was washed twice with water the organic phase was concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (solvent: hexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1 L three-necked flask fitted with a mechanical stirrer were added 36.9 g (162 mmol) of periodic acid and 150 ml of sulfuric acid. After periodic acid was dissolved, 80.7 g (486 mmol) of potassium iodide was added portionwise. The temperature of the content was cooled to 0° C. and 75.0 g (318 mmol) of 1,2-dibromobenzene was added. The resulting mixture was stirred at 0° C. for 30 minutes. After the reaction mixture was poured into ice, the whole was filtrated and a solid was taken out. The solid was recrystallized from THF/methanol twice to obtain white crystals of 1,2-dibromo-4,5-diiodobenzene (76.2 g, yield 49%). To a 1 L three-necked flask fitted with a mechanical stirrer After the reaction mixture was poured into ice the whole was filtrated The solid was recrystallized from THF/methanol twice