C1C2C3C=CC=CC=3SC=2C=CC=1.BrBr.O.S([O-])([O-])=O.[Na+].[Na+].Br[C:24]1[CH:37]=[CH:36][C:27]2[S:28][C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[C:26]=2[CH:25]=1>C(Cl)(Cl)Cl>[Br:35][C:32]1[CH:33]=[CH:34][C:29]2[S:28][C:27]3[CH:36]=[CH:37][CH:24]=[CH:25][C:26]=3[C:30]=2[CH:31]=1Dibenzothiophene (15 g, 79.9 mmol) was dissolved in 1.5 L chloroform. To the solution, bromine (12.76 g, 79.9 mmol) was added dropwise. The reaction mixture was vigorously stirring for 2 days at room temperature and then treated with sodium sulfite water solution. The organic phase was evaporated to give a white solid which has 48% unreacted dibenzothiophene, 50% 2-bromodibenbzothiophene and less 2% 2,8-dibromodibenzothiophene based on GC-MS and HPLC results. The mixture was repeatedly recrystallized with ethyl acetate to get pure 2-bromodibenzothiophene.
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