HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acrylonitrile → 3-Bromocinnamonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acrylonitrile | HCID 7855 | — |
| Reactant | Benzoyl chloride, 3-bromo- | HCID 74377 | — |
| Reactant | Tri(2-ethylhexyl)amine | HCID 102705 | — |
| Catalyst | Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II) | HCID 105144 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | 3-Bromocinnamonitrile | HCID 367319 | 9.9% |
Reaction Steps
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%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04335054 |
| Source dataset | uspto-grants-1982_06 |
| ORD ID | ord-c397fa561b0048608ff65610d05320f6 |
| Source note | uspto-grants-1982_06 |