Formic Acid → HCID 86668274, compound

HRID 2048125Notes

Reaction equation

HRID 2048125 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH:3]=[CH:2]2.I[C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1.N1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:23]=1.C(O)=O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:1]12([C:9]3[CH:14]=[CH:13][C:12]([C:18]45[CH2:19][CH:20]([CH2:22][CH2:23]4)[CH:21]=[CH:17]5)=[CH:11][CH:10]=3)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2

Participants

9

Reactant 5

HCID 284Formic AcidHCID 8082PiperidineHCID 8473NorbornadieneHCID 11776TriphenylphosphineHCID 12208p-Diiodobenzene

Product 1

HCID 86668274HCID 86668274, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,5-norbornadiene (2.6 g, 28.2 mmol) and p-diiodobenzene (1.5 g, 4.55 mmol) were dissolved in 5 mL of N,N-dimethylformamide (DMF). To the resulting solution were added 2.3 g (27.0 mmol) of piperidine as a base, 100 mg (0.45 mmol) of palladium acetate, and 0.36 g (1.37 mmol) triphenylphosphine as a ligand in an argon atmosphere, following which the solution was stirred. Formic acid (1.1 g, 23.9 mmol) was added at a time to this reaction solution by syringe, and reacted at 60° C. for 4 hours. In this reaction, a white mist vigorously arose due to neutralization. Following the reaction, extraction with ethyl acetate and rinsing with water were carried out, after which the solvent was removed. The residue thus obtained was column purified (Rf=0.45; eluant: hexane) with silica gel using an ethyl acetate/hexane (volumetric mixing ratio, 3/1) mixed solvent, thereby giving the difunctional monomer (1,4-bisnorbornenyl benzene) as a colorless solid (yield, 35%).

Workup

  1. customreacted at 60° C. for 4 hours
  2. customIn this reaction
  3. washrinsing with water
  4. customafter which the solvent was removed
  5. customThe residue thus obtained
  6. custompurified (Rf=0.45; eluant: hexane) with silica gel using an ethyl acetate/hexane (volumetric mixing ratio, 3/1)
  7. additionmixed solvent

Sources & evidence

ORD record
ord-f6602eab3e9a48d3a68bda3fccc91427
Source dataset
uspto-grants-2013_11
Patent number
US08592807B2

Reaction notes

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