Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | HCID 68196377 | HCID 68196377 | — |
| Reactant | HCID 178418373 | HCID 178418373 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68193220 | HCID 68193220 | 62% |
Reaction Steps
Ethyl (4′-bromobiphenyl-4-yl)(difluoro)acetate (0.10 g, 0.28 mmol) obtained in Example 30-(1) was dissolved in tetrahydrofuran (20 mL), and a solution of methylmagnesium iodide in diethyl ether (3.0 M, 1.0 mL, 3.0 mmol) was added under a nitrogen atmosphere at room temperature, followed by stirring at the same temperature for 5 hours. Hydrochloric acid (1 M) was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the extract was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.35 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.063 g, 0.18 mmol) as a yellow oil (yield 62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785462B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-bacd91d309ce4ce6bce9511d69a701f3 |
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| Source note | uspto-grants-2014_07 |
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