HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-[4-({3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}methyl)phenyl]ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(Bromomethyl)benzeneethanol | HCID 22337018 | — |
| Reactant | 3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol | HCID 66586265 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[4-({3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}methyl)phenyl]ethanol | HCID 66914254 | 75.1% |
Reaction Steps
To a stirred solution of 3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol (0.086 g, 0.28 mmol) and 2-(4-bromomethlyphenyl)ethanol (0.061 g, 0.28 mmol) in CH2Cl2 (5 mL) is added Cs2CO3 (0.365 g, 1.12 mmol). After 1.5 h, additional alkylating agent (0.015 g) is added and the reaction is stirred overnight. The reaction is neutralized with 2N aq HCl, extracted with ethyl acetate and dried (MgSO4). Chromatography eluting with 5:95 ethyl acetate:hexane afforded the title compound (0.092 g, 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576215B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-e0e0b693af6f46db9745ffadb48f7694 |
| Source note | uspto-grants-2009_08 |