Dimethylformamide → 3-Bromo-1,6-bis(4-methylphenyl)pyrene

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21]3[C:22]4=[C:23]5[C:18](=[CH:19][CH:20]=3)[CH:17]=[CH:16][C:15]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:14]5[CH:13]=[CH:12][C:11]4=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:31]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:31][C:17]1[CH:16]=[C:15]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:14]2[C:23]3=[C:22]4[C:11]([CH:10]=[CH:9][C:8]([C:5]5[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=5)=[C:21]4[CH:20]=[CH:19][C:18]=13)=[CH:12][CH:13]=2

Participants

Procedure

Next, a mixed solution of 2.6 g of 1,6-bis(4-methylphenyl)pyrene, 1.2 g of N-bromosuccinimide and 60 ml of dimethylformamide was stirred under a nitrogen gas stream at 60° C. for 5 hours. The solution was cooled to room temperature and 60 ml of water was poured into the solution, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. The resulting solid was recrystallized from toluene and then vacuum-dried to obtain 1.4 g of 3-bromo-1,6-bis(4-methylphenyl)pyrene.