Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | HCID 67252112 | HCID 67252112 | — |
| Catalyst | Cuprous chloride | HCID 62652 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86635683 | HCID 86635683 | 31% |
Reaction Steps
A solution of the 7-iodo-5-difluoromethoxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindolone (0.082 g, 0.16 mmol) in DMF (5 mL) was treated with CuCl (0.064 g, 0.65 mmol) and stirred at 140° C. for 1-2 h. After this time, the reaction mixture was diluted with dichloromethane (15 mL) and the solids removed by filtration. The filtrate was concentrated. Silica gel column chromatography using, typically 30% ethyl acetate in hexane, afforded 7-Chloro-2-(4-trifluoromethoxy-benzyl)-5-difluoromethoxy-2,3-dihydro-isoindolone (0.02 g, 31%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.08 (s, 2H), 4.58 (s, 2H), 6.37 (t, 1H), 6.87 (s, 1H), 7.01 (m, 3H), 7.17 (d, 2H). GC-MS: m/z 407 (M)+, 322 (M−85)+.
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-51d5e1c3a01849aeaf85cf6495cb33b5 |
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| Source note | uspto-grants-2011_06 |
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