Styrene → Stilbene

HRID 1876932Notes

Reaction equation

HRID 1876932 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>>[C:2]1([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7501StyreneHCID 8471TriethylamineHCID 11575Iodobenzene

Product 1

HCID 11502StilbeneYield 100%

Procedure

A solution of iodobenzene (1 mmol), of styrene (1.5 mmol), of PdBr2 or PdSO4 (10 mol %) and of triethylamine (2 mmol) in N,N′-butylmethylimidazolium methyl H-phosphonate (2 g) is brought to 110° C. for 5 hrs. The formed trans-stilbene is extracted with ether (3×10 mL), the structure of which is confirmed by 1H NMR. (yield=100%).

Workup

  1. extractionThe formed trans-stilbene is extracted with ether (3×10 mL)

Sources & evidence

ORD record
ord-e093f0bdceb44ee1970c8b4c5de52e09
Source dataset
uspto-grants-2012_11
Patent number
US08309736B2

Reaction notes

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