7-Benzyloxy-3-bromo-1,2-dihydronaphthalene
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Chemical Product Description & Applications
7-Benzyloxy-3-bromo-1,2-dihydronaphthalene is an unsaturated, oxygen-protected coupling fragment associated with elacestrant synthesis. The vinyl bromide enables borylation or carbon–carbon coupling, while the benzyl ether masks the aromatic phenol. Its partially saturated fused ring provides the framework later converted into the aryl-substituted tetralin portion of the target molecule.
The selected material is the brominated alkene, positioned after dehydration of a bromotetralol precursor. Replacing bromine with a boronate creates an alternative coupling partner without changing the protected ring system. Subsequent fragment coupling and reduction elaborate the carbon skeleton, while debenzylation restores the phenol at a later stage. These operations separate coupling-handle preparation from oxygen deprotection.
Typical Applications
- Dihydronaphthalenyl boronate preparation: Used in Miyaura borylation to replace the vinyl bromide with a boronate group, producing a protected fragment for subsequent cross-coupling.
- Elacestrant carbon-skeleton assembly: Used directly or through its boronate derivative to connect the protected dihydronaphthalene fragment with a complementary substituted aromatic partner.
Specifications
| Parameter | Specification | Test Method |
|---|---|---|
| Appearance | Solid; color consistent with the reference sample | Visual inspection |
| Identification | Consistent with authenticated reference | FTIR fingerprint comparison |
| Chromatographic purity | ≥98.0 area% | HPLC with suitable UV or CAD detection |
| Total organic impurities | ≤2.0 area% | HPLC, area normalization |
| Largest individual impurity | ≤1.0 area% | HPLC, area normalization |
| Water | ≤1.0% w/w | Karl Fischer titration |
Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.
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