HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Fluoride → 3-(4-tert-Butyl-phenyl)-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | 4-tert-Butylphenylboronic acid | HCID 2734320 | — |
| Reactant | 4-Cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester | HCID 68520808 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Bis(cyclopenta-2,4-dien-1-yl-di(propan-2-yl)phosphane);iron(2+) | HCID 15420033 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 3-(4-tert-Butyl-phenyl)-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester | HCID 68525497 | — |
Reaction Steps
Combine 4-cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester (0.136 mmol) with 4-t-butyl-phenyl boronic acid (0.163 mmol), palladium acetate (0.027 mmol), 1,1′-Bis(di-i-propylphosphino)ferrocene (0.027 mmol), and potassium fluoride in DME at room temperature. Stirred at room temperature for 17 hours. Concentrated reaction in vacuo and purified by radial chromatography eluting with hexanes/methylene chloride to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 7.41 (q, 4H, J=21.7 Hz), 4.26 (q, 2H, J=7.0 Hz), 1.37 (s, 9H) and 1.21 (t, 3H, J=7.3 Hz), 19F NMR (CDCl3) δ—57.2 ppm (s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07642361B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-f086890992e049a08f58009a853840a8 |
| Source note | uspto-grants-2010_01 |