Dibenzothiophene → 2-Bromodibenzothiophene

HRID 385306

Reaction equation

HRID 385306 reaction equation
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]=1

Participants

6

Reactant 4

HCID 3023Dibenzothiophene2×HCID 24408BromineHCID 6311202,8-DibromodibenzothiopheneHCID 86645562Sodium sulphite monohydrate

Product 1

HCID 2995082-Bromodibenzothiophene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15 g (79.9 mmol) dibenzothiophene was dissolved in 1.5 L chloroform. To the solution, 12.76 g (79.9 mmol) bromine was added dropwise. The reaction mixture was vigorously stirred 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.

Workup

  1. customThe organic phase was evaporated
  2. customto give a white solid which
  3. customresults
  4. customThe mixture was repeatedly recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-9b7a05676b124b72b0aa44077400e177
Source dataset
uspto-grants-2013_02
Patent number
US08367850B2

Linked notes

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