Styrene → trans-Stilbene

HRID 429608

Reaction equation

HRID 429608 reaction equation
C([O-])(=O)C.[Na+].Cl[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].CN(C=O)C>[C:7]1(/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:7]1(/[CH:13]=[CH:14]\[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:7]1([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH2:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 3

HCID 7501StyreneHCID 7964ChlorobenzeneHCID 517045Sodium Acetate

Product 3

HCID 107401,1-DiphenylethyleneYield 14.4%HCID 638088trans-StilbeneYield 84.9%HCID 5356785cis-StilbeneYield 0.7%

Reagents, catalysts & solvents 2

HCID 164911Tetraphenylphosphonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A reaction is performed as described in Example 1, except that 10.3 mg (0.04 mmol) of (CH3CN)2PdCl2, 59.7 mg (0.16 mmol) of Ph4PCl, 157.6 mg (1.92 mmol) of anhydrous sodium acetate, 107.1 mg (0.95 mmol) of chlorobenzene and 136.2 mg (1.31 mmol) of styrene in 1 ml of DMF are reacted. Stirring is performed at 150° C. for 8 hours. With 95.6% conversion of Cl-benzene, a 70.4% yield of Heck products (84.9% trans-stilbene, 0.7% cis-stilbene, and 14.4% 1,1-diphenylethene) is obtained.

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-a2489af76f8f455489a19371317c7868
Source dataset
uspto-grants-2001_11
Patent number
US06316675B1

Linked notes

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