Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | Benzeneacetonitrile, 2-fluoro- | HCID 67592 | — |
| Reactant | HCID 13459385 | HCID 13459385 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57827301 | HCID 57827301 | 67.2% |
Reaction Steps
Potassium tert-butoxide (9.93 g) was added to a solution of 2-fluorophenylacetonitrile (10 g), toluene-4-sulfonic acid 2-allyloxyethyl ester (19 g) and 18-crown-6 (3.91 g) in tetrahydrofuran (400 mL) under ice-cooling. The reaction solution was stirred at the same temperature for 10 minutes. The reaction solution was warmed to room temperature and further stirred for four hours. Aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (10.9 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08158620B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-576f8524a38d4d8eb9a0d36fee68ed8f |
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| Source note | uspto-grants-2012_04 |
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