2-tert-butylpyrene

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

Procedure: Next, a mixed solution of 45.0 g (content: 83%) of 2-t-butylpyrene, 660 ml of dichloromethane and 220 ml of methanol was cooled to 0° C. under an argon gas stream and then 56.4 g of benzyltrimethylammonium tribromide dissolved in 100 ml of dichloromethane was added dropwise. This mixed solution was stirred at room temperature for 2.5 hours and 5.64 g of benzyltrimethylammonium tribromide was added, followed by stirring for 1.5 hours. After the organic layer was isolated by pouring 250 ml of water into this mixed solution, the aqueous layer was extracted twice with 250 ml of dichloromethane. The combined organic layer was washed with 300 ml of water, dried over magnesium sulfate and then evaporated. To the resulting solid, 300 ml of methanol was added, followed by stirring and further filtration. To the resulting solid, 200 ml of hexane was added, and then the resulting solution was stirred, filtered and vacuum-dried to obtain 44.5 g of 1-bromo-7-t-butylpyrene. was added dropwise by stirring for 1.5 hours After the organic layer was isolated the aqueous layer was extracted twice with 250 ml of dichloromethane The combined organic layer was washed with 300 ml of water dried over magnesium sulfate evaporated To the resulting solid, 300 ml of methanol was added by stirring further filtration To the resulting solid, 200 ml of hexane was added the resulting solution was stirred filtered vacuum-dried

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

Procedure: A mixed solution of 100 g of pyrene, 55.4 g of t-butylchloride and 400 ml of dichloromethane was cooled to 0° C. under an argon gas stream and then 70.4 g of aluminum chloride was added. This mixed solution was stirred at room temperature for 5 hours and poured into 500 g of ice, followed by stirring at room temperature for 30 minutes. After the mixed solution was suction-filtered, the filtrate was extracted twice with 300 ml of dichloromethane. The organic layer was washed with 300 ml of water, dried over magnesium sulfate and then evaporated. To the concentrated residue, 300 ml of methanol was added, followed by stirring at 80° C. and further filtration. Furthermore, 300 ml of methanol was added, followed by stirring at 80° C. and further filtration. To 59.1 g of the crude product obtained by vacuum drying among 110.7 g of the crude product, 150 ml of methanol was added. The resulting solution was stirred at 85° C. for one hour, filtered and then vacuum-dried to obtain 50.3 g (content: 83%) of 2-t-butylpyrene. by stirring at room temperature for 30 minutes After the mixed solution was suction-filtered the filtrate was extracted twice with 300 ml of dichloromethane The organic layer was washed with 300 ml of water dried over magnesium sulfate evaporated To the concentrated residue, 300 ml of methanol was added by stirring at 80° C. further filtration Furthermore, 300 ml of methanol was added by stirring at 80° C. further filtration To 59.1 g of the crude product obtained by vacuum drying among 110.7 g of the crude product, 150 ml of methanol was added The resulting solution was stirred at 85° C. for one hour filtered vacuum-dried

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

Procedure: Next, a mixed solution of 3 g (content: 65%) of 2-t-butylpyrene, 50 ml of dichloromethane and 15 ml of methanol was cooled to 0° C. under a nitrogen gas stream and then 3.3 g of benzyltrimethylammonium tribromide dissolved in 10 ml of dichloromethane was added dropwise. This mixed solution was stirred at room temperature for 2 hours and 50 ml of water was poured into the solution, followed by extraction with 50 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. To the resulting solid, 10 ml of methanol was added, followed by stirring for 10 minutes and further filtration. Furthermore, 30 ml of hexane was added and, after stirring for 30 minutes, the solution was filtered and the filtrate was vacuum-dried to obtain 2.3 g of 1-bromo-7-t-butylpyrene. was added dropwise followed by extraction with 50 ml of dichloromethane The organic layer was washed twice with 50 ml of water dried over magnesium sulfate evaporated To the resulting solid, 10 ml of methanol was added by stirring for 10 minutes further filtration Furthermore, 30 ml of hexane was added after stirring for 30 minutes the solution was filtered the filtrate was vacuum-dried

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

Procedure: A mixed solution of 4.1 g of pyrene, 2 g of t-butylchloride and 33 ml of dichloromethane was cooled to 0° C. under a nitrogen gas stream and then 2.7 g of aluminum chloride was added. This mixed solution was stirred at room temperature for 3 hours and 30 ml of water was poured into the solution, followed by extraction with 30 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 3 g (content: 65%) of 2-t-butylpyrene. followed by extraction with 30 ml of dichloromethane The organic layer was washed twice with 20 ml of water dried over magnesium sulfate evaporated The concentrate was purified by silica gel column chromatography vacuum-dried

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

Procedure: A mixed solution of 3 g of 2-tert-butylpyrene (65% content), 50 ml of dichloromethane and 15 ml of methanol was then cooled to 0° C. under a nitrogen stream, and a solution of 3.3 g of benzyltrimethylammonium tribromide in 10 ml of dichloromethane was added dropwise to the mixed solution. After the mixed solution was stirred at room temperature for 2 hours, 50 ml of water was added thereto, and the mixture was extracted with 50 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate, and then evaporated. Ten ml of methanol was added to the resulting solid and stirred for 10 minutes, and then the solid was separated by filtration. Thereafter, 30 ml of hexane was further added to the solid and stirred for 30 minutes, and then the solid was separated by filtration. The solid was dried under vacuum to give 2.3 g of 1-bromo-7-tert-butylpyrene. the mixture was extracted with 50 ml of dichloromethane The organic layer was washed twice with 50 ml of water dried over magnesium sulfate evaporated Ten ml of methanol was added to the resulting solid stirred for 10 minutes the solid was separated by filtration Thereafter, 30 ml of hexane was further added to the solid stirred for 30 minutes the solid was separated by filtration The solid was dried under vacuum

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

Procedure: A mixed solution of 4.1 g of pyrene, 2 g of tert-butyl chloride and 33 ml of dichloromethane was cooled to 0° C. under a nitrogen stream, and 2.7 g of aluminum chloride was added thereto. After the mixed solution was stirred at room temperature for 3 hours, 30 ml of water was added thereto, and the mixture was extracted with 30 ml of dichloromethane. The organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography and dried under vacuum to give 3 g of 2-tert-butylpyrene (65% content). was added the mixture was extracted with 30 ml of dichloromethane The organic layer was washed twice with 20 ml of water dried over magnesium sulfate evaporated The resulting residue was purified by silica gel column chromatography dried under vacuum

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixed solution of 120 g (content 79.2%) of 2-t-butylpyrene, and 3000 ml of tetrahydrofuran was added 69.66 g of N-bromosuccinimide under a nitrogen stream. This mixed solution was stirred at 30° C. for about 3 hours, and concentrated, 500 ml of methanol was added, and the mixture was stirred for about 1 hour, and filtered. To the resulting solid was added 500 ml of hexane, and the mixture was heated and stirred for about 1 hour, and filtered. After the resultant was vacuum dried, 106.9 g of 1-bromo-7-t-butylpyrene was obtained. concentrated 500 ml of methanol was added the mixture was stirred for about 1 hour filtered To the resulting solid was added 500 ml of hexane the mixture was heated stirred for about 1 hour filtered dried

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

Procedure: A mixed solution of 150 g of pyrene, 75.52 g of t-butyl chloride and 742 ml of dichloromethane was cooled to 0° C. under a nitrogen stream, and 98.9 g of aluminum chloride was added. After this mixed solution was stirred at room temperature for 3 hours, 1100 ml of water was added, and this was extracted with 1100 ml of dichloromethane. The organic layer was washed with 750 ml of water three times, dried with magnesium sulfate, and evaporated, and this was purified by methanol washing, and filtered. After the resultant was vacuum dried, 272 g (content 79.2%) of 2-t-butylpyrene was obtained. was added this was extracted with 1100 ml of dichloromethane The organic layer was washed with 750 ml of water three times dried with magnesium sulfate evaporated this was purified by methanol washing filtered dried

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

Procedure: Then, a mixed solution of 3 g (content 65%) of 2-t-butylpyrene, 50 ml of dichloromethane and 15 ml of methanol was cooled to 0° C. under a nitrogen stream, and 3.3 g of benzyltrimethylammonium tribromide dissolved in 10 ml of dichloromethane was added dropwise. After this mixed solution was stirred at room temperature for 2 hours, 50 ml of water was added, and this was extracted with 50 ml of dichloromethane. The organic layer was washed with 50 ml of water two times, dried with magnesium sulfate, and evaporated. To the resulting solid was added 10 ml of methanol, and the mixture was stirred for 10 minutes, and filtered. Further, 30 ml of hexane was added, and the mixture was stirred for 30 minutes, and filtered. After the resultant was vacuum dried, 2.3 g of 1-bromo-7-t-butylpyrene was obtained. was added dropwise this was extracted with 50 ml of dichloromethane The organic layer was washed with 50 ml of water two times dried with magnesium sulfate evaporated To the resulting solid was added 10 ml of methanol the mixture was stirred for 10 minutes filtered Further, 30 ml of hexane was added the mixture was stirred for 30 minutes filtered dried

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

Procedure: A mixed solution of 4.1 g of pyrene, 2 g of t-butyl chloride and 33 ml of dichloromethane was cooled to 0° C. under a nitrogen stream, and 2.7 g of aluminum chloride was added. After this mixed solution was stirred at room temperature for 3 hours, 30 ml of water was added, and this was extracted with 30 ml of dichloromethane. The organic layer was washed with 20 ml of water two times, dried with magnesium sulfate, and evaporated. This was purified by silica gel column chromatography, and vacuum-dried to obtain 3 g (content 65%) of 2-t-butylpyrene. was added this was extracted with 30 ml of dichloromethane The organic layer was washed with 20 ml of water two times dried with magnesium sulfate evaporated This was purified by silica gel column chromatography vacuum-dried