trans-beta-Bromostyrene → trans-Stilbene

HRID 2182833

Reaction equation

HRID 2182833 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/Br)=[CH:3][CH:2]=1.[I-].[C:11]1([Zn+])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Pd].C(F)(F)(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F.C(#N)C.C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:4]1(/[CH:7]=[CH:8]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

8

Reactant 2

HCID 5314126trans-beta-Bromostyrene2×HCID 178506617HCID 178506617, compound2×

Product 1

HCID 638088trans-Stilbene

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 9639PerfluorohexaneSolvent

Procedure

In an illustrative example, a coupling reaction was conducted between (E)-2-bromostyrene (PhCH═CHBr) and phenylzinc iodide (PhZnI) promoted by a fluorous palladium catalyst. The catalyst was prepared from Pd2(dba)3 and the known fluorous phosphine (p-C6F13CH2CH2C6H4)3P. A mixture of the catalyst in FC-72 was contacted in a U-tube with a first organic phase containing (E)-2-bromostyrene in acetonitrile and a second organic phase containing phenylzinc iodide in THF. After one day at ambient temperature, each organic phase was removed and subjected to standard aqueous workup. Unreacted (E)-2-bromostyrene was recovered from the first organic phase while the coupled reaction product, (E)-stilbene (PhCH═CHPh) was isolated from the second organic phase.

Workup

  1. customeach organic phase was removed
  2. customwas recovered from the first organic phase while the coupled reaction product

Sources & evidence

ORD record
ord-4807387aed194981af52ac32c94e23b4
Source dataset
uspto-grants-2005_05
Patent number
US06897331B2

Linked notes

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