Nitrogen → 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Temperatur

100 °C

To a 250 mL reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), copper(I) iodide (0.644 g, 3.38 mmol) and cesium carbonate (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 h. The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite. The Celite was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtOAc/Hex) yielded 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole as an off white solid (3.78 g, 12.27 mmol, 72.6%): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) δ −58.04; EIMS m/z 307.

1. customTo a 250 mL reaction flask
2. temperatureThe reaction was cooled to room temperature
3. filtrationfiltered through a plug of Celite
4. washThe Celite was further washed with EtOAc
5. additionWater was added to the combined organics, and the layers
6. customwere separated
7. extractionfurther extracted with EtOAc
8. concentrationThe combined organics were concentrated in vacuo
9. customPurification via flash chromatography (silica/EtOAc/Hex)

ORD-Eintrag

ord-0b225df869074c4c9877773f93546227

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09440964B2