Toluene → Carbazole

HRID 2221157Notes

Reaction equation

HRID 2221157 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-526b04bcc4f04206b5956bef1ec84e8c
Source dataset
uspto-grants-2008_05
Patent number
US07368509B2

Reaction notes

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