HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 57949631, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | p-Xylyl bromide | HCID 7721 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-bromo-2,3-dihydro-1H-isoindol-1-one | HCID 22607119 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 57949631 | HCID 57949631 | 79.1% |
Reaction Steps
5-Bromo-2,3-dihydro-isoindol-1-one (1.0 g, 4.72 mmol), 1-bromomethyl-4-methyl-benzene (1.14 g, 6.14 mmol) and cesium carbonate (3.08 g, 9.44 mmol) were suspended in anhydrous NMP (10 mL). The mixture was immersed in a 60° C. oil bath for 16.5 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Column chromatography (20% to 40% ethyl acetate/hexanes) provided the title compound as a yellow solid (1.18 g, 79%). 1H NMR CDCl3: 7.76 (d, 1H), 7.62 (d, 1H), 7.55 (s, 1H), 4.76 (s, 2H), 4.24 (s, 2H), 2.35 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07968570B2 |
| Source dataset | uspto-grants-2011_06 |
| ORD ID | ord-b122c51bb8004871a36e9d54b42d6ccf |
| Source note | uspto-grants-2011_06 |