Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Reactant | 4-Bromo-3-(trifluoromethyl)aniline | HCID 67852 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 40044612 | HCID 40044612 | 67.1% |
Reaction Steps
N,N-Diisopropylethylamine (1.22 ml, 7.00 mmol) and methyl bromoacetate (1.00 g, 6.54 mmol) were sequentially added to a solution of 4-bromo-3-(trifluoromethyl)aniline (1.40 g, 5.83 mmol) in DMF (10 ml), and the mixture was heated with stirring at 80° C. for 25 hours. The reaction mixture was cooled and water was then added, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was triturated with hexane:dichloromethane=9:1 to give (4-bromo-3-trifluoromethyl-phenylamino)-acetic acid methyl ester (1.22 g, 67%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09169254B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-e95a5bf121e24d65a3bdaba272ed158e |
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| Source note | uspto-grants-2015_10 |
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