2,2'-Bipyridine → Carbazole

HRID 2221159Notes

Reaction equation

HRID 2221159 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.C(Br)Br.[CH:16]12CC(CC1)C=[CH:17]2.C=CC1C=CC=CC=1>C1(C)C=CC=CC=1>[CH:10]1[C:9]2[NH:8][C:7]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:17]=2[CH:16]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14742,2'-BipyridineHCID 7501StyreneHCID 69201635HCID 69201635, compound

Product 1

HCID 6854Carbazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To an ampoule, Cu(I)Br (1 mmol), 2,2′-bipyridine (1 mmol), norbornene methylene bromide (NBMBr) (1 mmol) and styrene (St) (100 mmol) were added in 10 mL toluene. The heterogeneous mixture was placed under vacuum and degassed via a freeze-pump-thaw cycle thrice. After degassing, the reaction mixture in ampoule was stirred at 100° C. for 12 hrs. The macromonomer containing polystyrene segments (NBMPStBr) was precipitated from methanol. Polymer was dissolved in THF and reprecipitated from methanol three times. Number average molecular weight of (NBMPStBr) is 160000 and PDI is 1.28(by GPC).

Workup

  1. customdegassed via a freeze-pump-thaw cycle thrice
  2. customAfter degassing
  3. additionThe macromonomer containing polystyrene segments (NBMPStBr)
  4. customwas precipitated from methanol
  5. dissolutionPolymer was dissolved in THF
  6. customreprecipitated from methanol three times

Sources & evidence

ORD record
ord-f8c88d3374d74c149e47711a5e037423
Source dataset
uspto-grants-2008_05
Patent number
US07368508B2

Reaction notes

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