Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Boron tribromide dichloromethane | HCID 22277759 | — |
| Reactant | HCID 58047676 | HCID 58047676 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58047066 | HCID 58047066 | 88% |
Reaction Steps
To a solution of N-(1-{5-[2-(4-methoxyphenyl)ethyl]-1-benzofuran-2-yl}ethyl)acetamide (922 mg, 2.73 mmol) obtained in Example 156 in methylene chloride (50 mL) was added 1M boron tribromide-methylene chloride solution (5.46 mL, 5.46 mmol) at −78° C., and the mixture was stirred at the same temperature for 4 hr. The reaction mixture was warmed to 0° C., and methanol was added thereto. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from hexane-ethyl acetate to give the title compound (774 mg, yield 88%) as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08501804B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-3802ffb7cd76422795d3cf6ef8c952cb |
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| Source note | uspto-grants-2013_08 |
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