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

Temperature

100 °C

To a 250 mL reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and 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 hours (h). The reaction wascooled to room temperature (RT), 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 column chromatography using EtOAc/hexanes as eluent provided the title compound as an off-white solid (3.78 g, 73%): 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 ([M]+).

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

ORD record

ord-bc7be61ccb5c44baa9d8f3dc326cff54

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376401B2