Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tert-Butylamine | HCID 6385 | — |
| Reactant | Bromine | HCID 24408 | — |
| Reactant | 2-Benzyloxyphenol | HCID 80459 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67346586 | HCID 67346586 | — |
Reaction Steps
Tert-butyl amine (2 eq) was dissolved in toluene (1M) and the solution was cooled to −30° C. Br2 (1 eq) was added dropwise maintaining the temperature. The mixture was left stirring for 30 min, then it was cooled to −78° C. A solution of 2-benzyloxyphenol (1 eq) in DCM (6M) was added dropwise. The mixture was allowed to reach RT over the course of 3 h. The mixture was diluted with Et2O and H2O was added. The mixture was washed with 1N HCl, sat. aq. Na2S2O3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residue was purified by FC (PE:EtOAc, 9:1). The colourless oil was used without further characterization in the next reaction. (ES−) m/z 277, 279 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07989438B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-ed42c8da1d974888b95032826daae174 |
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| Source note | uspto-grants-2011_08 |
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