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

HRID 1270662Notes

Reaction equation

HRID 1270662 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].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]

Participants

7

Reactant 4

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

Product 1

HCID 866000185-Butylnorbornene 5-norbornene-2-carboxylic acid butyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

5-Butylnorbornene (730 g) and 5-norbornene-2-carboxylic acid butyl ester (940 g) were added to a reactor at room temperature. Then, toluene (1,600 g) was added to the reactor. The air inside the reactor was replaced by nitrogen and the reactor was heated to 90° C. Then, palladium diacetate (0.21 g), dimethyl aniliniumtetrakis (pentafluorophenyl)borate (1.55 g) and tricylcohexylphosphine (0.27 g) dissolved in dichloromethyl were added to the reactor. Reaction was performed for 18 hours while stirring to obtain a polymer solution.

Workup

  1. additionwere added to the reactor
  2. customReaction
  3. customto obtain a polymer solution

Sources & evidence

ORD record
ord-45f737c0c5824ce1a33c22ee2566cec1
Source dataset
uspto-grants-2007_04
Patent number
US07202312B2

Reaction notes

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