HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2374682Generated: October 30, 2026
Dimethylformamide → Methyl 4-cyano-2-fluorobenzoate
https://huagongshe.com/reaction/2374682
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 anhydrous N,N-dimethylformamide (100 mL) was purged with nitrogen and the mixture 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 solid was purified on silica gel using 1:5 ethyl acetate/hexane to afford the title compound (6.1 g, 80%). MS (DCI): m/z 180 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07462724B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-0ffb61fcded345929de38e2b3f75dd7e |
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| Source note | uspto-grants-2008_12 |
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