Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzenamine, 3-bromo-4-methyl- | HCID 82187 | — |
| Reactant | Ethanol, 1-bromo- | HCID 14202443 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 63333977 | HCID 63333977 | 62.3% |
Reaction Steps
Triethylamine (0.28 mL, 2.00 mmol) and bromoethanol (0.14 mL, 1.98 mmol) were added to a solution of 3-bromo-4-methyl-phenylamine (240 mg, 1.29 mmol) in toluene (2 ml). The mixture was stirred at 100° C. overnight and H2O was then added, followed by extraction with AcOEt (×2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt) to give 2-(3-bromo-4-methyl-phenylamino)-ethanol (185 mg, 62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09169254B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-df06129f810d4fa78261f028e46c3f96 |
|---|
| Source note | uspto-grants-2015_10 |
|---|