Acrylonitrile → 4-Bromocinnamonitrile

HRID 1284868

Reaction equation

HRID 1284868 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[C:9](#[N:12])[CH:10]=[CH2:11]>[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:11]=[CH:10][C:9]#[N:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 115221-Bromo-4-iodobenzene

Product 1

HCID 534804-BromocinnamonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure described in Example 47 is repeated, but using 7.07 g (25 mmols) of 4-bromoiodobenzene and 1.83 g (27.5 mmols) of acrylonitrile. After a reaction time of 8 hours at 130° C., 3.95 g (19.0 mmols) of 4-bromocinnamonitrile are obtained, corresponding to a yield of 76% of theory (conversion figure 7600; Pd content 0.01 mol %).

Sources & evidence

ORD record
ord-8ab49296290e4657888114bf4a135ce1
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Linked notes

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