HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl trifluoroacetate → HCID 117942077, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl trifluoroacetate | HCID 9794 | — |
| Reactant | 4-bromo-2-methyl-1H-1,3-benzodiazole | HCID 15828979 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 117942077 | HCID 117942077 | — |
Reaction Conditions
| Temperature | -78 °C |
|---|
Reaction Steps
4-Bromo-2-methyl-1H-benzimidazole (500 mg, 2.37 mmol) was dissolved in THF (8 mL) and cooled to −78° C. n-Butyllithium (2.3 mL, 2.5 M in hexanes, 5.7 mmol) was added dropwise and the reaction was stirred at −78° C. for 30 min. Trifluoroacetic acid ethyl ester (339 μL, 2.8 mmol) was added and the reaction was stirred at 0° C. for 1 h. The reaction was quenched with HCl (2 N, 4 mL), then extracted with water and EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase silica gel column chromatography (CH2Cl2/MeOH/NH4OH) provided 2,2,2-trifluoro-1-(2-methyl-1H-benzoimidazol-4-yl)-ethanone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09199994B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-256a140ccdec41728bb3dabaf625b3cc |
| Source note | uspto-grants-2015_12 |