Toluene → Carbazole

HRID 132705Notes

Reaction equation

HRID 132705 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:13]1(C)C=CC=C[CH:14]=1>>[CH:10]1[C:9]2[NH:8][C:7]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 14742,2'-Bipyridine

Product 1

HCID 6854Carbazole

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-e5c8cc683b0442abb743d28cd38e6ff6
Source dataset
uspto-grants-2008_06
Patent number
US07388055B2

Reaction notes

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