Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 23114260 | HCID 23114260 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 23114199 | HCID 23114199 | 96.2% |
Reaction Steps
To a solution of N-(3-(4-isopropyl-3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (500 mg, 1.18 mmol) obtained in Example 185 in dichloromethane (5 mL) was added dropwise at −70° C. under an argon atmosphere boron tribromide (1.0 M, dichloromethane solution, 2.36 mL, 2.36 mmol) and the resulting mixture was gradually warmed to room temperature. Water was added to the reaction solution and the product was extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 465 mg (yield: 96%) of the title compound. Melting point: 220-221° C. (ethyl acetate-hexane).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07465815B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-add840e8c50d4f25b8164c9749bf32d2 |
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| Source note | uspto-grants-2008_12 |
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