Styrene → trans-Stilbene

HRID 429611

Reaction equation

HRID 429611 reaction equation
[C:1]([O-])(=O)[CH3:2].[Na+].[CH2:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].CN(C=O)C>[C:8]1(/[CH:7]=[CH:6]/[C:1]2[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:8]1(/[CH:7]=[CH:6]\[C:1]2[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:8]1([C:7]([C:1]2[CH:2]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH2:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 2

HCID 7501StyreneHCID 517045Sodium Acetate

Product 3

HCID 107401,1-DiphenylethyleneYield 14.5%HCID 638088trans-StilbeneYield 85%HCID 5356785cis-StilbeneYield 0.5%

Reagents, catalysts & solvents 2

HCID 164911Tetraphenylphosphonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A reaction is performed as described in Example 1, except that 3.9 mg (0.015 mmol) of (CH3CN)2PdCl2, 34.9 mg (0.09 mmol) of Ph4PCl, 520.9 mg (6.35 mmol) of anhydrous sodium acetate, 499.6 mg (3.118 mmol) of Br-benzene and 489.3 mg (4.7 mmol) of styrene are reacted in 1.5 ml of DMF. Stirring is performed at 130° C. for 5 hours. According to the processing described in Example 1, a 74.8% yield of Heck products (85.0% trans-stilbene, 0.5% cis-stilbene, and 14.5% 1,1-diphenylethene) is obtained with 74.6% conversion of Br-benzene.

Sources & evidence

ORD record
ord-1d4146d68dbd45f885d469d03ee4ecc5
Source dataset
uspto-grants-2001_11
Patent number
US06316675B1

Linked notes

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