HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → HCID 59233267, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-(2-Bromoethoxy)tetrahydro-2H-pyran | HCID 86621 | — |
| Reactant | 5-Bromo-2-hydroxybenzonitrile | HCID 2757014 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59233267 | HCID 59233267 | 97.1% |
Reaction Steps
A solution of 5-bromo-2-hydroxybenzonitrile (1 g, 5.05 mmol) in DMF was treated with 95% NaH (242 mg, 9.6 mmol) for 20 min at room temperature. 2-(2-Bromoethoxy)tetrahydro-2H-pyran (0.839 ml, 5.56 mmol) was then added to the reaction and the mixture was stirred at room temperature for 5 hrs. The reaction was then diluted with DCM and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated to dryness to provide the crude title compound, 5-bromo-2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)benzonitrile (1.6 g, 9.75% yield) which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178534B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-08a74c9b35ad476389a7ff44765a884f |
| Source note | uspto-grants-2012_05 |