Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Boron tribromide dichloromethane | HCID 22277759 | — |
| Reactant | HCID 58047331 | HCID 58047331 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 136167104 | HCID 136167104 | 100.2% |
Reaction Steps
To a suspension of N-[1-(6-methoxy-1,2-benzisoxazol-3-yl)ethyl]acetamide (500 mg, 2.13 mmol) obtained in Reference Example 9 in toluene (10 mL) was added 1 M boron tribromide methylene chloride solution (6.40 mL, 6.40 mmol) under ice-cooling and, under a nitrogen atmosphere, the mixture was stirred at room temperature for 1 hr. Methylene chloride (5 mL) and 1 M boron tribromide methylene chloride solution (5.00 mL, 5.00 mmol) were added thereto at room temperature, and the mixture was stirred under heating at 50° C. for 16 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (470 mg, quantitative) as an oil. This was used for the next step without purification.
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-692284e77b58450d8b3a2b038a470555 |
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| Source note | uspto-grants-2013_08 |
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