HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-bromo-1-(2-ethoxyethyl)-1H-pyrazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Bromopyrazole | HCID 16375 | — |
| Reactant | (4-(1-(1-Ethoxyethyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate | HCID 57868870 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-bromo-1-(2-ethoxyethyl)-1H-pyrazole | HCID 51892139 | 108.4% |
Reaction Steps
To a solution of 4-bromopyrazole (21, 70.0 g, 0.476 mol) in CH2Cl2 (600 mL) was added a solution of 3.1 M HCl in dioxane (4 mL) and ethyl vinyl ether (18, 41 g, 0.569 mol, 1.2 equiv). The resulting reaction mixture was stirred at room temperature for 3 hrs. The reaction was quenched with aqueous NaHCO3 and the two layers were separated. The organic layer was washed with water, dried over Na2SO4, and concentrated under reduced pressure to dryness to afford 4-bromo-1-(ethoxyethyl)-1H-pyrazole (22, 113 g, 104.3 g theoretical, 97% yield) as an oily (GC purity: 89%), which was directly used in the subsequent reaction without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410265B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-f2ac5b3c6b264db9a850edd6d3fe60d7 |
| Source note | uspto-grants-2013_04 |