2,2'-Bipyridine → HCID 68545727, compound

HRID 1264145Notes

Reaction equation

HRID 1264145 reaction equation
N1C=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=CN=1.BrCC1C=CC(CBr)=CC=1.[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:26])[CH:24]=[CH2:25].[CH2:32]=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>[Cu]Br>[CH2:5]=[CH:4][C:3]1[CH:2]=[CH:7][CH:12]=[CH:11][CH:10]=1.[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:26])[CH:24]=[CH2:25].[CH2:32]=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 14742,2'-BipyridineHCID 7501Styrene2×HCID 8846Butyl AcrylateHCID 693351,4-Bis(bromomethyl)benzene

Product 1

HCID 68545727HCID 68545727, compound

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Conditions

Temperature
100 °C

Procedure

To a 10 ml round bottom flask with a stir bar, 2,2′-bipyridine (32.8 mg, 0.21 mmol), copper (I) bromide (10.2 mg, 0.07 mmol), and α,α′-dibromo-p-xylene (18.5 mg, 0.07 mmol) were added. The flask was sealed with a rubber septum and the contents of the flask degassed by applying a vacuum and backfilling with argon. Degassed butyl acrylate (5.0 ml, 34.9 mmol) was added via syringe. The reaction mixture was heated at 100° C. and stirred. After six hours the reaction was viscous. Conversion was found to be 89% by 1H NMR; Mn=57,300, Mw/Mn=1.4. The reaction was cooled to 50° C. and then placed under vacuum to remove residual butyl acrylate. After 2 hours, degassed styrene (2.3 ml, 21 mmol) was added via syringe and the reaction heated to 100° C. After 12 h, the reaction was stopped. Conversion of the styrene was 85%; Mn=75,200, Mw/Mn=1.4. The polymer was purified by dissolving in THF and passing over alumina, followed by repeated precipitation into methanol. 1H NMR showed that the polymer contained 28% styrene.

Workup

  1. customThe flask was sealed with a rubber septum
  2. customthe contents of the flask degassed
  3. temperatureThe reaction was cooled to 50° C.
  4. customto remove residual butyl acrylate
  5. waitAfter 2 hours
  6. additionwas added via syringe
  7. temperaturethe reaction heated to 100° C
  8. waitAfter 12 h
  9. customThe polymer was purified
  10. dissolutionby dissolving in THF
  11. customprecipitation into methanol

Sources & evidence

ORD record
ord-7fbf4528b6d44bdb979493f2b8ae4527
Source dataset
uspto-grants-2003_04
Patent number
US06541580B1

Reaction notes

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