HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 634372Generated: October 30, 2026
Hydrochloric Acid → HCID 118131158, compound
https://huagongshe.com/reaction/634372
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 118131086 | HCID 118131086 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | HCID 118131158 | HCID 118131158 | 81.2% |
Reaction Steps
To a solution of 4-bromo-3-(1-hydroxyethyl)-7-methyl-1H-isochromen-1-one (intermediate A4, 1.04 g, 3.67 mmol) in Dioxane/H2O (5:1) (60 ml), phenylboronic acid (0.67 g, 5.51 mmol) and Na2CO3 (0.779 g, 7.34 mmol) were added followed by Pd(dppf)Cl2 (0.269 g, 0.367 mmol) and the resulting mixture was heated at 90° C. for 2 hrs. 1N HCl was added (pH≈2) and the mixture was partitioned between EtOAc and water. The organic phase was washed twice with brine and dried over sodium sulfate. The solvent was removed under vacuum and the crude was purified by flash column chromatography on Biotage silica gel cartridge (cyclohexane:EtOAc=95:5 to 40:60) to afford title compound as a yellow oil (0.835 g, 2.98 mmol, 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09321776B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-fb303f6bcf514f41a701275c8445aaa0 |
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| Source note | uspto-grants-2016_04 |
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