p-Bromochlorobenzene → 4-Chlorostyrene

HRID 1284866Notes

Reaction equation

HRID 1284866 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[C:9]([O-])(=O)[CH3:10].[Na+]>[Pd].CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:9]=[CH2:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7806p-BromochlorobenzeneHCID 517045Sodium Acetate

Product 1

HCID 140854-ChlorostyreneYield 52.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2 ml of the stock solution described in Example 23 are added to 18 ml of DMF. 9.77 g (50 mmols) of 4-chlorobromobenzene and 4.52 g (55 mmols) of anhydrous sodium acetate are then added. The reaction mixture is then placed under ethylene in a pressure apparatus and is stirred for 6 hours at 10 bar and 130° C. 3.62 g (26.1 mmols) of 4-chlorostyrene are obtained, corresponding to a yield of 52% of theory (conversion figure 5200; Pd content 0.01 mol %).

Sources & evidence

ORD record
ord-97387ec6a7b9418eb3316fe71451b632
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

Loading…