HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 241438Generated: November 1, 2026
Water → Methyl 5-cyano-2-(trifluoromethyl)benzoate
https://huagongshe.com/reaction/241438
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | 5-Chloro-2-(trifluoromethyl)benzoic acid methyl ester | HCID 46311110 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | di-palladium (II) tris(dibenzylideneacetone) | HCID 11170526 | — |
| Catalyst | Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+) | HCID 15826098 | — |
| Product | Methyl 5-cyano-2-(trifluoromethyl)benzoate | HCID 71060125 | 66.5% |
Reaction Steps
Dissolve methyl 5-chloro-2-(trifluoromethyl)benzoate (500 mg, 2.1 mmol), zinc (II) cyanide (197 mg, 1.68 mmol), zinc (55 mg, 0.84 mmol), di-palladium (II) tris(dibenzylideneacetone) (192 mg, 0.21 mmol), and diphenylphosphino ferrocene (233 mg, 0.42 mmol) in dimethylacetamide (20 mL). Heat the reaction mixture to 85° C., and stir for 12 hours. Pour the resulting mixture into water, and extract with EtOAc (2×100 mL). Dry the combined organics over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the residue by silica gel chromatography eluting with 50:1 petroleum ether:EtOAc to give the title compound (320 mg, 66.5% yield) as a white solid. 1H NMR (300 MHz, CDCl3,) δ 8.09 (s, 1H), 7.90 (s, 2H), 3.80 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08648200B2 |
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| Source dataset | uspto-grants-2014_02 |
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| ORD ID | ord-2311be9f0c484a85a8b17538c4045416 |
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| Source note | uspto-grants-2014_02 |
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