Methane → Stilbene

HRID 53469

Reaction equation

HRID 53469 reaction equation
C.Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C=O)C.C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.[Pd]>[C:3]1([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 297MethaneHCID 7501StyreneHCID 7961Bromobenzene

Product 1

HCID 11502StilbeneYield 74.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 82707Tetrabutylammonium AcetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a miniautoclave, 85 mg of palladium on active charcoal (similar to Example 59, metal content 5%) are suspended in 20 ml of DMF. After 2 mmol of bromobenzene, 2 mmol of styrene, and 4 mmol of tetrabutylammonium acetate have been added, heating at 120° C. is performed with shaking. After 16 h, 267 mg of stilbene can be isolated from the reaction solution. This corresponds to a 74% conversion.

Sources & evidence

ORD record
ord-002a23bbff254801b64735d02f6b6ee5
Source dataset
uspto-grants-1997_04
Patent number
US05620584

Linked notes

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