HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Hydroxybenzaldehyde → 4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Hydroxybenzaldehyde | HCID 126 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Bromo-5-(trifluoromethyl)pyridine | HCID 2736434 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehyde | HCID 26985700 | 84.1% |
Reaction Steps
4-hydroxybenzaldehyde (4.094 mmol, 1 eq), 2-bromo-5-(trifluoromethyl)pyridine (4.094 mmol, 1 eq) and potassium carbonate (6.142 mmol, 1.5 eq) were suspended in N,N-dimethylformamide (15 ml). The reaction mixture was irradiated by microwave Biotage Initiator at 130° C. for 30 min. Reaction mixture was diluted with EtOAc (15 ml) and extraction with water followed (3×15 ml). Organic layers were combined, washed with brine, dried over MgSO4, filtered and evaporated giving 4-(5-trifluoromethyl-pyridin-2-yloxy)-benzaldehyde (3.443 mmol, yield=84%, purity=94%). [M+H]+=268.25 1H NMR (300 MHz, DMSO-d6) δ/ppm 7.33-7.38 (m, 1H), 7.43 (d, J=8.5 Hz, 2H), 7.99 (d, J=8.7 Hz, 2H), 8.26-8.33 (m, 1H), 8.57-8.62 (m, 1H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637536B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-832c8ea95a9441d59e86d96821e0b05f |
| Source note | uspto-grants-2014_01 |