HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(4-Formyl-2-methoxy-phenoxy)4-trifluoromethyl-benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | 2-(3-Bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile | HCID 21930341 | — |
| Catalyst | HCID 178506421 | HCID 178506421 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 2-(4-Formyl-2-methoxy-phenoxy)4-trifluoromethyl-benzonitrile | HCID 21930456 | 14% |
Reaction Steps
Under nitrogen, 2-(3-bromo-4-formyl-phenoxy)-4-trifluoromethyl-benzonitrile (0.87 g, 2.6 mmol), phenylboronic acid (336 mg, 2.7 mmol), 1,1′-bis(diphenyl)phospino-ferrocene palladium (9 mg, 0.13 mmol) and sodium carbonate (331 mg, 3.1 mmol) in dimethoxyethane:water:ethanol solution (7:3:2, 10 mL) was stirred at 60° C. for 6 h and then at 40° C. for 16 h. The mixture was then poured over water, extracted into ethyl acetate, and dried over MgSO4. The crude material was chromatographed on an ISCO CombiFlash Chromatography System to yield 2-(4-formyl-2-methoxy-phenoxy)-4-trifluoromethyl-benzonitrile as a clear oil (117 mg, 14%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07119122B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-c7c58a6413724d8d8066796fd078f490 |
| Source note | uspto-grants-2006_10 |