Acrylonitrile → 3-Bromocinnamonitrile

HRID 1156458

Reaction equation

HRID 1156458 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=O.[C:11](#[N:14])[CH:12]=C.C(C(CCCC)CN(CC(CC)CCCC)CC(CC)CCCC)C>C(#N)CC.[Pd+2]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH:5]=[CH:12][C:11]#[N:14]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 74377Benzoyl chloride, 3-bromo-HCID 102705Tri(2-ethylhexyl)amine

Product 1

HCID 3673193-BromocinnamonitrileYield 9.9%

Reagents, catalysts & solvents 2

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)CatalystHCID 7854PropionitrileSolvent

Procedure

The procedure described in Example 1 is repeated, except that 21.94 g (0.1 mol) of 3-bromobenzoyl chloride, 6.63 g (0.125 mol) of acrylonitrile, 35.37 g (0.1 mol) of tris-(2-ethylhexyl)-amine and 0.3046 g (0.001 mol) of bis-acetylacetonato)-palladium(II) in 50 ml of propionitrile are used. After a reaction time of 3 hours at 100° C., 2.05 g (0.0099 mol) of 3-bromocinnamonitrile are obtained, corresponding to a yield of 9.9% of theory; melting point 62° C. Analysis for C9H6NBr (molecular weight 208): calculated C 51.96%, H 2.91%, N 6.73%; found C 52.29%, H 2.95%, N 6.91%.

Sources & evidence

ORD record
ord-c397fa561b0048608ff65610d05320f6
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Linked notes

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