Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-Fluoropyridine | HCID 9746 | — |
| Reactant | Ethyl trifluoroacetate | HCID 9794 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 53416101 | HCID 53416101 | 90% |
Reaction Steps
Lithium diisopropylamide (8.2 mL, 14.8 mmol, 1.8M in heptane) was added to THF (20 mL) cooled to −78° C. in a dry ice/acetone bath. 2-Fluoropyridine (1.07 mL, 12.4 mmol) was added dropwise, and the resulting mixture was stirred at −78° C. for 3 hours. Ethyl trifluoroacetate (2.06 mL, 17.2 mmol) was added to the suspension dropwise. The reaction mixture was allowed to slowly warm to room temperature. After 1 hour, the mixture was poured into 1M hydrochloric acid (35 mL) and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over magnesium sulfate, filtered, and evaporated to yield the hydrate of 2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethanone (1.9 g, 90%) as a semisolid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394795B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-eb4535dd93dc422a954a9280eac158c6 |
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| Source note | uspto-grants-2013_03 |
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