HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 2-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Chloro-5-(trifluoromethyl)pyridine | HCID 92342 | — |
| Reactant | 3-Bromo-5-methylphenol | HCID 12648409 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine | HCID 66876906 | 85.2% |
Reaction Conditions
| Temperature | 110 °C |
|---|
Reaction Steps
To a solution of 3-bromo-5-methylphenol (2.0 g, 0.0106 mol) in DMF (15 mL) was added K2CO3 (2.93 g, 0.02 mol) at RT. 2-Chloro-5-(trifluoromethyl)pyridine (1.94 g, 0.0106 mol) was added and the reaction was refluxed at 110° C. for 12 h. The reaction mixture was quenched with water and extracted with EtOAc three times. The total organic extract was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (3 g, 84.5%). 1H NMR (500 MHz, CDCl3): δ 8.45 (s, 1H), 7.92 (d, J=8.6 Hz, 1H), 7.26 (d, J=14.95 Hz, 1H), 7.13 (s, 1H), 7.03 (d, J=10 Hz, 1H), 6.90 (s, 1H), 2.36 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08044052B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-026251bf2d3c480580b3d6a5c473e5ca |
| Source note | uspto-grants-2011_10 |