HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Methyl 4-cyano-2-fluorobenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Bromo-2-fluoro-benzoic acid methyl ester | HCID 11345311 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | Methyl 4-cyano-2-fluorobenzoate | HCID 15278726 | 80% |
Reaction Steps
A solution of methyl 4-bromo-2-fluorobenzoate (10.0 g, 43 mmol), zinc cyanide (10.0 g, 86 mmol) and palladium tetrakis(triphenylphosphine) (2.5 g, 0.64 mmol) in N,N-dimethylformamide (100 mL) was stirred at 80° C. overnight. After cooling, the mixture was partitioned between ethyl acetate and brine and the organic phase washed with water and concentrated. The residue was purified by flash chromatography on silica gel (1:5 ethyl acetate/hexane) to afford 6.1 g (80%) of the title compound. MS (DCI): m/z 180 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07999117B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-3fa1746c03924152bc039014cecdfa8a |
| Source note | uspto-grants-2011_08 |