HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Benzoic acid, 3-chloro-5-cyano-, methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Methyl 3-chloro-5-fluorobenzoate | HCID 21942504 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Benzoic acid, 3-chloro-5-cyano-, methyl ester | HCID 21942517 | — |
Reaction Steps
A mixture of the methyl 3-chloro-5-fluorobenzoate, zinc cyanide (8.46g, 72.3 mmol) zinc (dust, 235 mg, 3.6 mmol), [1,1′bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex with dichloromethane (1:1) (1.5 g, 1.8 mmol) in N,N-dimethylformamide (70 ml) was heated at reflux for 1 hour. The reaction was cooled to ambient temperature and diluted with ethyl acetate. The organic solution was extracted with water and brine and concentrated in vacuo, to afford crude methyl 3-chloro-5-cyanobenzoate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06660753B2 |
| Source dataset | uspto-grants-2003_12 |
| ORD ID | ord-1efa043914e74c2687dd3828bb3fc117 |
| Source note | uspto-grants-2003_12 |