Toluene → 5-Norbornene 2-allylacetate 5-butylnorbornene 5-norbornene-2-carboxylic methylester

HRID 1160024Notes

Reaction equation

HRID 1160024 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH2:2]2.[CH2:8]([CH2:11][C:12]([O-:14])=[O:13])[CH:9]=[CH2:10].[CH2:15]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)[CH2:16][CH2:17][CH3:18].[CH3:26][O:27][C:28]([CH:30]1[CH2:35][CH:34]2[CH2:36][CH:31]1[CH:32]=[CH:33]2)=[O:29].C1(C)C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].C(O)C>[CH:1]12[CH2:7][CH:4]([CH:3]=[CH:2]1)[CH2:5][CH2:6]2.[CH2:8]([CH2:11][C:12]([O-:14])=[O:13])[CH:9]=[CH2:10].[CH2:15]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)[CH2:16][CH2:17][CH3:18].[CH3:26][O:27][C:28]([CH:30]1[CH2:35][CH:34]2[CH2:36][CH:31]1[CH:32]=[CH:33]2)=[O:29]

Participants

8

Reactant 4

HCID 1140Toluene2×HCID 168020Bicyclo[2.2.1]hept-2-ene, 5-butyl-HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 865975875-Norbornene 2-allylacetate

Product 1

HCID 866039015-Norbornene 2-allylacetate 5-butylnorbornene 5-norbornene-2-carboxylic methylester

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

5-norbornene-2-allylacetate (5 mL, 30.9 mmol), 5-butylnorbornene (1.2 mL, 6.6 mmol), 5-norbornene-2-carboxylic methylester (1 mL, 6.6 mmol) and toluene (12.4 mL) were charged into a 250 mL Schlenk flask. Pd(OAc)2 (0.66 mg, 2.94 μmol) and [(Cy)3PH][(B(C6F5)4) (5.65 mg, 5.88 μmol) were dissolved in CH2Cl2 (1 mL) and added to the monomer solution. While the reaction mixture was stirred for 18 hours at 90° C., the reaction mixture became viscous. After the reaction was completed, 120 ml of toluene was added to the viscous solution to dilute it. The solution was poured into an excess of ethanol to precipitate a white polymer, which was filtered through a glass funnel, washed with ethanol, and dried in vacuo at 80° C. for 24 hours to yield 5-norbornene-2-allylacetate/5-butylnorbornene/5-norbornene-2-carboxylic methylester polymer (6.45 g: 90.5% by weight based on the total weight of used monomers). The weight average molecular weight (Mw) of the polymer was 211,891 and Mw/Mn was 2.67.

Workup

  1. additionadded to the monomer solution
  2. additionto dilute it
  3. customto precipitate a white polymer, which
  4. filtrationwas filtered through a glass funnel
  5. washwashed with ethanol
  6. customdried in vacuo at 80° C. for 24 hours

Sources & evidence

ORD record
ord-73911c09baf34fb89d312d7a9b4426db
Source dataset
uspto-grants-2010_10
Patent number
US07814713B2

Reaction notes

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