Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Fluoroethyl bromide | HCID 12982 | — |
| Reactant | 4-Amino-2-(trifluoromethyl)benzonitrile | HCID 522170 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 57633709 | HCID 57633709 | 79.8% |
Reaction Steps
To a solution of 4-amino-2-(trifluoromethyl)benzonitrile (0.100 g, 0.54 mmol) in acetonitrile (3 mL) was added cesium carbonate (0.438 g, 1.34 mmol) and 1-bromo-2-fluoroethane (0.340 g, 2.68 mmol). The mixture was heated in a microwave at 120° C. for 15 min. Upon cooling, additional 1-bromo-2-fluoroethane (0.340 g, 2.68 mmol) was added and the reaction was heated in the microwave at 140° C. for 20 min. Upon cooling, the solids were filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by radial chromatography (10-40% ethyl acetate-hexane gradient) to give 0.100 g of a mixture (6:1) of the title compound and 4-[bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile as a white solid, which was used as such in the next reaction.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07514470B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-32bfd6bb643b4fa7b42884e7c154abd5 |
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| Source note | uspto-grants-2009_04 |
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