HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2041821Generated: October 29, 2026
1,10-Phenanthroline → 2-(4-Bromophenyl)benzo(d)oxazole
https://huagongshe.com/reaction/2041821
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,10-Phenanthroline | HCID 1318 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromoaniline | HCID 11992 | — |
| Reactant | 4-Bromobenzoyl chloride | HCID 68515 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-(4-Bromophenyl)benzo(d)oxazole | HCID 12846715 | 87% |
Reaction Steps
A mixture of 4-bromobenzoylchloride (4.84 g, 22 mmol), 2-bromoaniline (3.8 g, 22 mmol), CuI (0.21 g, 1.1 mmol), Cs2CO3 (14.3 g, 44 mmol) and 1,10-phenathroline (0.398 g, 2.2 mmol) in anhydrous 1,4-dioxane (80 mL) was degassed and heated at about 125° C. under argon overnight. The mixture was cooled and poured into ethyl acetate (˜200 mL) and filtered. The filtrate was absorbed on silica gel, purified by column chromatography (hexanes/ethyl acetate 4:1), and precipitated by hexanes to give a white solid (5.2 g, in 87% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586205B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-9b884ce1a97f4193935dea93c92a06d0 |
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| Source note | uspto-grants-2013_11 |
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