Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | 7-Bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol | HCID 135418373 | — |
| Catalyst | copper(I) bromide | HCID 24593 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 135409725 | HCID 135409725 | 60% |
Reaction Steps
A mixture of 7-bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol (100 mg, 0.33 mmol), and copper(I) bromide (56 mg, 0.39 mmol) in anhydrous N,N dimethylformamide (1.5 mL) was stirred with freshly prepared sodium methoxide (15 wt % in methanol, 1 ml) and heated to 120° C. for 4 h. The mixture was cooled and diluted with HCl (1N, 5 ml). Isolation of the crude product with ethyl acetate followed by flash chromatography (40%-50% EtOAc/petroleum ether) gave the title compound as an off-white solid (50 mg, 60% yield, mp 225-228° C.); MS m/e 258 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06794403B2 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-26858c666f184842b12a72d328352927 |
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| Source note | uspto-grants-2004_09 |
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