Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phthalimidine | HCID 10199 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | 1-(Bromomethyl)-4-chlorobenzene | HCID 69329 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57949578 | HCID 57949578 | 97% |
Reaction Steps
A mixture of 2,3-dihydro-isoindol-1-one (0.133 g, 1 mmol,), 1-bromomethyl-4-chloro-benzene (0.246 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-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.125 g, 97%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.24 (s, 2H), 4.76 (s, 2H), 7.22-7.54 (m, 7H), 7.90 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07968570B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-4a364f23bc2d41e194c3ba345474550e |
|---|
| Source note | uspto-grants-2011_06 |
|---|