Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | 2-(Bromomethyl)benzonitrile | HCID 89599 | — |
| Reactant | 6-Fluoro-2,3-dihydro-7-iodo-1H-isoindol-1-one | HCID 67251916 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67252195 | HCID 67252195 | 41% |
Reaction Steps
A mixture of 6-fluoro-7-iodo-2,3-dihydro-isoindol-1-one (0.070 g, 0.25 mmol), 1-bromomethyl-2-cyano-benzene (0.059 g, 0.3 mmol), Cs2CO3 (0.098 g, 0.3 mmol), and 18-crown-6 (0.007 g, 0.025 for mmol) in acetone (5 mL) was stirred at 70° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 6-fluoro-7-iodo-2-(2-cyano-benzyl)-2,3-dihydro-isoindol-1-one (0.040 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.33 (s, 2H), 5.04 (s, 2H), 7.04-7.71 (m, 6H), GC-MS: m/z 392 (M)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07968570B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-cfdf56d1094a42f0a999d59f304524a2 |
|---|
| Source note | uspto-grants-2011_06 |
|---|
