Methyl Acrylate → HCID 66855655, compound

HRID 1042454Notes

Reaction equation

HRID 1042454 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CC([O-])=O.[K+].[CH:23]12[CH2:29][CH:26](CC1)C=C2.[C:30]([O:34][CH3:35])(=[O:33])[CH:31]=[CH2:32].I[CH2:37][CH2:38][CH3:39].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:35][O:34][C:30](=[O:33])[CH:31]=[CH:32][C:2]1[C:7]([CH2:37][CH2:38][CH3:39])=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:23][CH2:29][CH3:26]

Participants

10

Reactant 7

HCID 7294Methyl AcrylateHCID 103522-NorborneneHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 336431-IodopropaneHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 517044Potassium Acetate

Product 1

HCID 66855655HCID 66855655, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

In a 100 ml flask, 4-iodobenzotrifluoride (1 g, 3.68 mmol) was dissolved in 10 ml DMF, and Pd(OAc)2 (165 mg, 0.2 eq), K2CO3 (2.54 g, 5.0 eq), KOAc (1.8 g, 5.0 eq), norbornylene (692 mg, 1.0 eq), methyl acrylate (0.33 ml, 1.0 eq), and iodopropane (3.75 g, 6.0 eq) were added stepwisely at room temperature. The resulting reaction mixture was stirred for 3 days. After the completion of the reaction, the Na2S2O3 solution was poured into the reaction mixture, which was stirred for 30 minutes, extracted with EtOAc 50 ml (3 times), and dried with anh. MgSO4. The organic layer was filtered, concentrated in vacuo, and purified with column chromatography (Hexane: EtOAc=8:1) to give the title compound (0.343 g, 30%).

Workup

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction
  3. stirringwas stirred for 30 minutes
  4. extractionextracted with EtOAc 50 ml (3 times)
  5. dry with materialdried with anh. MgSO4
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated in vacuo
  8. custompurified with column chromatography (Hexane: EtOAc=8:1)

Sources & evidence

ORD record
ord-7cb83448059a4d6e816fb8eb40a69595
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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