Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Bromo-3-fluorobenzotrifluoride | HCID 142414 | — |
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Ammonium Hydroxide | HCID 14923 | 0.1% |
| Product | HCID 86687409 | HCID 86687409 | 44.5% |
Reaction Steps
A solution of 1H-imidazole (0.420 g, 6.17 mmol) in 12 mL dioxane was treated with sodium ethoxide (0.441 g, 6.48 mmol) and was allowed to stir for 30 minutes. 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene (0.885 ml, 6.17 mmol) was added and the reaction mixture was heated to 120° C. in a sealed vial overnight. The reaction mixture was poured into water and was extracted with EtOAc. The organics were concentrated and purified directly by reverse phase column chromatography [RediSep Gold C-18 100 g (Teledyne Isco, Lincoln, Nebr.), 10 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] yielding 1-(2-bromo-5-(trifluoromethyl)phenyl)-1H-imidazole (0.400 g, 1.374 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051311B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-f3ea4bdf3c9046368d21e37f68bbae8c |
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| Source note | uspto-grants-2015_06 |
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