Tricyclohexylphosphine → 5-Butylnorbornene 5-norbornene-2-carboxylic acid butyl ester 5-norbornene-2-carboxylic acid methyl ester

HRID 1270663

Reaktionsgleichung

Reaktionsgleichung von HRID 1270663
[CH2:1]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)[CH2:2][CH2:3][CH3:4].[CH2:12]([O:16][C:17]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)=[O:18])[CH2:13][CH2:14][CH3:15].[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].FC1C([B-](C2C(F)=C(F)C(F)=C(F)C=2F)(C2C(F)=C(F)C(F)=C(F)C=2F)C2C(F)=C(F)C(F)=C(F)C=2F)=C(F)C(F)=C(F)C=1F.C[NH+](C)C1C=CC=CC=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(C)C=CC=CC=1>[CH2:1]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)[CH2:2][CH2:3][CH3:4].[CH2:12]([O:16][C:17]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)=[O:18])[CH2:13][CH2:14][CH3:15].[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]

Komponenten

8

Edukt 5

HCID 75806TricyclohexylphosphineHCID 168020Bicyclo[2.2.1]hept-2-ene, 5-butyl-2×HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate2×HCID 10996402N,N-dimethylanilinium tetrakis(pentafluorophenyl)borateHCID 15608148Butyl bicyclo[2.2.1]hept-5-ene-2-carboxylate2×

Produkt 1

HCID 866000195-Butylnorbornene 5-norbornene-2-carboxylic acid butyl ester 5-norbornene-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5-Butylnorbornene (35.8 g), 5-norbornene-2-carboxylic acid butyl ester (31.1 g) and 5-norbornene-2-carboxylic acid methyl ester (60.9 g) were added to a reactor at room temperature. Toluene (95.8 g) was added to the reactor. Air inside the reactor was replaced by nitrogen and the reactor was heated to 90° C. Palladium diacetate (22.4 mg), dimethyl aniliniumtetrakis (pentafluorophenyl)borate (160.2 mg) and tricylcohexylphosphine (28 mg) dissolved in dichloromethyl were added to the reactor. Reaction was performed for 18 hours while stirring to obtain a tricopolymer solution comprising 30 mol % of 5-butylnorbornene, 20 mol % of 5-norbornene-2-carboxylic acid butyl ester and 50 mol % of 5-norbornene-2-carboxylic acid methyl ester monomers. 287 g of toluene was added to dilute the solution. The copolymer had a molecular weight (Mw) of 175,000. The proportion of Mw/Mn was 2.13.

Aufarbeitung

  1. additionwere added to the reactor
  2. customReaction
  3. customto obtain a tricopolymer solution
  4. additionto dilute the solution

Quellen und Nachweise

ORD-Eintrag
ord-87ea5941c15a42f28171da8ceea4405a
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202312B2

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