Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-Fluorobenzylamine | HCID 67326 | — |
| Reactant | Methyl 2-(bromomethyl)-6-iodobenzoate | HCID 11268261 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 57949765 | HCID 57949765 | 40% |
Reaction Steps
A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.200 g, 0.56 mmol), 4-fluoro-benzylamine (0.7 mmol), and IC2CO3 (0.166 g, 1.2 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(4-fluoro-benzyl)-7-iodo-2,3-dihydro-isoindol-1-one (0.082 g, 40%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.16 (s, 2H), 4.75 (s, 2H), 7.01 (t, 2H), 7.28-7.40 (m, 4H), 7.89 (d, 1H). GC-MS: m/z 367 (M)+.
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-581b39d91bb64c1781012f4a1eddb8bd |
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| Source note | uspto-grants-2011_06 |
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