Styrene → trans-Stilbene

HRID 429612

Reaction equation

HRID 429612 reaction equation
C([O-])(=O)C.[Na+].[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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:16]/[C:15]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:19]1(/[CH:18]=[CH:17]\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:19]1([C:18]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

9

Reactant 3

HCID 7501StyreneHCID 214133-BromoquinolineHCID 517045Sodium Acetate

Product 4

HCID 107401,1-DiphenylethyleneYield 14.1%HCID 214133-BromoquinolineHCID 638088trans-StilbeneYield 85.1%HCID 5356785cis-StilbeneYield 0.8%

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 (CH2CN)2PdCl2, 34.9 mg (0.09 mmol) of Ph4PCl, 496.0 mg (6.05 mmol) of anhydrous sodium acetate, 638.74 mg (3.07 mmol) of 3-bromoquinoline and 427.0 mg (4.1 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 72.5% yield of Heck products (85.1% trans-stilbene, 0.8% cis-stilbene, and 14.1% 1,1-diphenylethene) is obtained with 78.5% conversion of 3-bromoquinoline.

Sources & evidence

ORD record
ord-dd08380619e74406b89f84d676a720ba
Source dataset
uspto-grants-2001_11
Patent number
US06316675B1

Linked notes

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