Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 4-Bromo-3-fluorobenzotrifluoride | HCID 142414 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86687409 | HCID 86687409 | 53.3% |
Reaction Steps
A microwave vial charged with potassium tert-butoxide (1.108 g, 9.88 mmol), 1H-imidazole (0.672 g, 9.88 mmol), 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.180 ml, 8.23 mmol), and 10 mL dioxane was heated to 180° C. in the microwave for 2 hours. LC/MS showed mostly product, so the reaction mixture was poured into water and was extracted with DCM. The organics were dried over MgSO4 and concentrated. The crude residue was purified by silica gel column chromatography (0 to 100% EtOAc/heptane) yielding 1-(2-bromo-5-(trifluoromethyl)phenyl)-1H-imidazole (1.277 g, 4.39 mmol, 53.3% yield). m/z (ESI) 291.9 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09012443B2 |
|---|
| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-5b6008d4138547a8acd0b4fc9ccbe250 |
|---|
| Source note | uspto-grants-2015_04 |
|---|