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

HRID 1270664

Reaction equation

HRID 1270664 reaction equation
[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]

Participants

8

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

5-Butylnorbornene (9.8 kg), 5-norbornene-2-carboxylic acid butyl ester (8.5 kg) and 5-norbornene-2-carboxylic acid methyl ester (16.7 kg) were added to a reactor at room temperature. Toluene (26.3 kg) was added to the reactor. Air inside the reactor was replaced by nitrogen and the reactor was heated to 90° C. Palladium diacetate (6.2 g), dimethyl aniliniumtetrakis (pentafluorophenyl)borate (44.1 g) and tricylcohexylphosphine (7.7 g) 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. 43.9 kg of toluene was added to dilute the solution.

Workup

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

Sources & evidence

ORD record
ord-7d9d09ca1ae54b189c048f595094b186
Source dataset
uspto-grants-2007_04
Patent number
US07202312B2

Linked notes

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