Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acrylate | HCID 8821 | — |
| Reactant | 2-Bromobenzonitrile | HCID 16272 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 53973261 | HCID 53973261 | 44.6% |
Reaction Steps
0.67 ml of the stock solution from Example 52, 3.05 g (16.8 mmols) of 2-bromobenzonitrile, 1.99 ml (18.4 mmols) of ethyl acrylate and 1.50 g (18.4 mmols) of anhydrous sodium acetate are added, under argon, to 16.3 ml of DMF, and the reaction mixture is stirred at 130° C. for 3 hours. After working up as described in Example 1, the crude product is recrystallised from a mixture of pentane and carbon tetrachloride. 1.5 g (7.5 mmols) of ethyl o-cyanocinnamate are obtained in the form of white crystals of melting point 56° C., corresponding to a yield of 44% of theory (conversion figure 4400; Pd content 0.01 mol %). Analysis for C12H11NO2 (molecular weight 201.23): calculated C 71.63; H 5.51; N 6.96; O 15.90, found C 71.17; H 5.64; N 6.88; O 16.56.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04564479 |
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| Source dataset | uspto-grants-1986_01 |
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| ORD ID | ord-d34ab9753d13471a8fbb446ecac07201 |
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| Source note | uspto-grants-1986_01 |
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