HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1690257Generated: November 2, 2026
1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- → Methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(thiophen-3-yl)propanoate
https://huagongshe.com/reaction/1690257
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- | HCID 79244 | — |
| Reactant | Methyl 3-thienylacetate | HCID 94041 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(thiophen-3-yl)propanoate | HCID 59161752 | — |
Reaction Steps
To pure methyl 2-(thiophen-3-yl)acetate (E41) in THF cooled to −78° C. was added LiHMDS, and the solution stirred at −78° C. for 30 min. Then N-(bromomethyl)phthalimide was added directly, and the solution was allowed to warm to 0° C. The mixture was poured into NaHCO3 (sat), extracted with EtOAc, dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 0-40% EtOAc/Hex) gave pure methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(thiophen-3-yl)propanoate (E45).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08153656B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-4540f5bccf3e40859e48746d210945d0 |
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| Source note | uspto-grants-2012_04 |
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