Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | HCID 86621240 | HCID 86621240 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86621239 | HCID 86621239 | 40% |
Reaction Steps
A 0.4 M solution of 3-(2-bromo-phenyl)-2-formylamino-acrylic acid ethyl ester (5.3 g; 17.8 mM) in anhydrous CH2Cl2, at 0° C., is added with N-bromosuccinimide (3.48 g; 19.6 mM). The mixture is left to slowly warm to room temperature. The reaction is completed in about 5 hours 30 mm. The equivalent amount of triethylamine is added drop by drop; after 30 minutes the mixture is washed with a NaHCO3 saturated solution and then with a NaCl saturated solution. The organic phase is dried over Na2SO4, the solid is filtered off and the clear solution is evaporated under reduced pressure to a residue. The crude (brownish oil) is purified by flash chromatography, using a 6:4 v/v mixture of hexane and ethyl acetate as eluent, thereby obtaining 2.68 g of 3-bromo-3-(2-bromo-phenyl)-2-formylamino-acrylic acid ethyl ester (white-pale yellow solid). (Yield: 40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07301027B2 |
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| Source dataset | uspto-grants-2007_11 |
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| ORD ID | ord-07359ccf0fb5470d85222ba37c7da62b |
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| Source note | uspto-grants-2007_11 |
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