Ethyl Acetate → 2-bromo-1-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]ethan-1-one

Temperature

75 °C

To a solution of 1-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-ethanone (10 g, 65.3 mmol) in acetic acid (1 mL) and THF (100 mL) was added a solution of PTT (phenyltrimethylammonium tribromide, 24.5 g, 65.3 mmol) in THF (100 mL) over 20 min. The reaction mixture was heated at 75° C. before cooling to RT. The resultant mixture was concentrated in vacuo and the products partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo to give a residue which was subjected to flash chromatography (SiO2, gradient 0 to 20% ethyl acetate in cyclohexane) to give 2-Bromo-1-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-ethanone as an oil (5.4 g, 36%). 1H NMR δ (ppm) (CDCl3): 7.98 (1 H, s), 5.53-5.42 (1 H, m), 4.69 (2 H, s), 1.52 (6 H, d, J=6.63 Hz).

1. temperaturebefore cooling to RT
2. concentrationThe resultant mixture was concentrated in vacuo
3. customthe products partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
4. customThe organic layer was separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a residue which

ORD record

ord-8a5e3d7ff0e74bdc9c696415ab44afd1

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09198918B2