Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phthalimidine | HCID 10199 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | 4-Methoxybenzyl bromide | HCID 165021 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 13929299 | HCID 13929299 | 63% |
Reaction Steps
A mixture of 2,3-dihydro-isoindol-1-one (0.133 g, 1 mmol), 1-bromomethyl-4-methoxy-benzene (0.222 g, 1.2 mmol,), Cs2CO3 (0.816 g, 2.5 mmol), and 18-crown-6 (0.026 g, 0.1 mmol) in acetone (5 mL) was stirred at 70° C. for 16 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.080 g, 63%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.80 (s, 3H), 4.24 (s, 2H), 4.76 (s, 2H), 6.88 (d, 2H), 7.25 (d, 2H), 7.36-7.52 (m, 3H), 7.90 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07968570B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-8837e8edd29746b08b9ebe311ec6742a |
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| Source note | uspto-grants-2011_06 |
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