Styrene → trans-Stilbene

HRID 429609

Reaction equation

HRID 429609 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:3]1(/[CH:2]=[CH:1]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:3]1(/[CH:2]=[CH:1]\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:3]1([C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7501StyreneHCID 7964Chlorobenzene

Product 3

HCID 107401,1-DiphenylethyleneYield 12.4%HCID 638088trans-StilbeneYield 86.7%HCID 5356785cis-StilbeneYield 0.9%

Conditions

Temperature
150 °C

Procedure

A reaction is performed as described in Example 1, except that 102.8 mg (0.99 mmol) of styrene and 164.8 mg (1.46 mmol) of chlorobenzene are used, and the reaction mixture is stirred at 150° C. for 5.5 hours. With 94.6% conversion of Cl-benzene, an 82.1% yield of Heck products (86.7% trans-stilbene, 0.9% cis-stilbene, 12.4% 1,1-diphenylethene) is obtained.

Sources & evidence

ORD record
ord-0f3dd49aeb5e4d00b6d810eb17ec34cb
Source dataset
uspto-grants-2001_11
Patent number
US06316675B1

Linked notes

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