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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1270663Generated: October 25, 2026

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

https://huagongshe.com/reaction/1270663

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTricyclohexylphosphineHCID 75806—
ReactantBicyclo[2.2.1]hept-2-ene, 5-butyl-HCID 168020—
ReactantMethyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 250075—
ReactantN,N-dimethylanilinium tetrakis(pentafluorophenyl)borateHCID 10996402—
ReactantButyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 15608148—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
Product5-Butylnorbornene 5-norbornene-2-carboxylic acid butyl ester 5-norbornene-2-carboxylic acid methyl esterHCID 86600019—

Reaction Conditions

Temperature90 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07202312B2
Source datasetuspto-grants-2007_04
ORD IDord-87ea5941c15a42f28171da8ceea4405a
Source noteuspto-grants-2007_04