HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-Bromo-2-(4-fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)imidazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | 4,5-dibromo-2-(4-fluorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole | HCID 18515956 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Bromo-2-(4-fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)imidazole | HCID 18515974 | 98% |
Reaction Steps
4,5-Dibromo-2-(4-fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)imidazole (10.8 g; 25 mmol) are dissolved in THF (108 ml) and cooled to −78 C under argon. N-BuLi (15.6 ml; 1.6 M) is added under stirring within 15 min. After 30 min at −78 C, isopropanol (7.8 ml; 0.1 mol) is introduced dropwise and the mixture warmed to room temperature. Water is added to the reaction mixture and the aqueous phase extracted three times with ethyl acetate. The combined organic phases are washed with saturated NaCl-solution, dried over Na2SO4, filtered and evaporated to dryness, yielding the title compound as colorless oil (9.1 g; 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06579874B2 |
| Source dataset | uspto-grants-2003_06 |
| ORD ID | ord-27ec40cfa6434e8c8dd5011caf528aad |
| Source note | uspto-grants-2003_06 |