Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Borane | HCID 6331 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 46314741 | HCID 46314741 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 39231616 | HCID 39231616 | 62.5% |
Reaction Steps
To a solution of 5-cyano-2-fluorobiphenyl (1.96 g) in tetrahydrofuran (35 mL), a solution of borane in tetrahydrofuran (1 M, 35 mL) was added dropwise at room temperature, and the mixture was stirred for 22 hours. Hydrochloric acid (1 M, 7 mL) was gradually added dropwise to the reaction solution, and the mixture was stirred for 2 hours. A 2 M aqueous sodium hydroxide solution was added thereto for separation into organic and aqueous layers. The aqueous layer was subjected to extraction with ethyl acetate. All the organic layers were combined, dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: hexane/ethyl acetate) to obtain the title compound (1.25 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206168B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-3ba5773ad8c443199cdc6da7595911db |
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| Source note | uspto-grants-2015_12 |
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