HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2259509Generated: November 3, 2026
1,2-Dibromobenzene → 3-(2-Bromophenyl)-1-(3-(((2-tetrahydropyranyl)oxy)methyl)phenyl)-1-propanone
https://huagongshe.com/reaction/2259509
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dibromobenzene | HCID 11414 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 1-(3-(((2-Tetrahydropyranyl)oxy)methyl)phenyl)-2-propen-1-ol | HCID 19002940 | — |
| Reactant | lithium;acetate;dihydrate | HCID 178526966 | — |
| Catalyst | Tetrabutylammonium Chloride | HCID 70681 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(2-Bromophenyl)-1-(3-(((2-tetrahydropyranyl)oxy)methyl)phenyl)-1-propanone | HCID 19002910 | — |
Reaction Steps
A mixture of the allylic alcohol of Example 1, Step 11, (30.14 g, 121 mmol), 1,2-dibromobenzene (16 mL), Pd(OAc)2 (830 mg), LiCl (5.38 g), LiOAc.2H2O (31.6 g), and Bu4NCl (67.96 g) in 240 mL of DMF was degassed and heated to 85° C. under N2 for 30 min and at 90° C. for 45 min. It was then added to ice and 25% aq. NH4OAc (2 L). The title ketone was extracted in EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:hexane 10:90; yield: 29.53 g (60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05472964 |
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| Source dataset | uspto-grants-1995_12 |
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| ORD ID | ord-0f25bd43f76942dca77dfc49744755cc |
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| Source note | uspto-grants-1995_12 |
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